Merge pull request 'beta' (#10) from beta into master

Reviewed-on: #10

.gitignore

@@ -9,6 +9,11 @@ output/
 data/
 logs/
 
+# Environment and secrets
+.env
+admin_password.txt
+logs/admin_password.txt
+
 # Python
 __pycache__/
 *.py[cod]
@@ -37,3 +42,6 @@ Thumbs.db
 
 # Docker
 .dockerignore
+
+#mounted dirs
+configs/

Dockerfile

@@ -23,8 +23,8 @@ RUN git clone https://github.com/robertdavidgraham/masscan /tmp/masscan && \
 WORKDIR /app
 
 # Copy requirements and install Python dependencies
-COPY requirements.txt .
-COPY requirements-web.txt .
+COPY app/requirements.txt .
+COPY app/requirements-web.txt .
 RUN pip install --no-cache-dir -r requirements.txt && \
     pip install --no-cache-dir -r requirements-web.txt
 
@@ -33,18 +33,19 @@ RUN pip install --no-cache-dir -r requirements.txt && \
 RUN playwright install chromium
 
 # Copy application code
-COPY src/ ./src/
-COPY templates/ ./templates/
-COPY web/ ./web/
-COPY migrations/ ./migrations/
-COPY alembic.ini .
-COPY init_db.py .
+COPY app/src/ ./src/
+COPY app/templates/ ./templates/
+COPY app/web/ ./web/
+COPY app/migrations/ ./migrations/
+COPY app/alembic.ini .
+COPY app/init_db.py .
+COPY app/docker-entrypoint.sh /docker-entrypoint.sh
 
 # Create required directories
 RUN mkdir -p /app/output /app/logs
 
 # Make scripts executable
-RUN chmod +x /app/src/scanner.py /app/init_db.py
+RUN chmod +x /app/src/scanner.py /app/init_db.py /docker-entrypoint.sh
 
 # Force Python unbuffered output
 ENV PYTHONUNBUFFERED=1

LICENSE

@@ -0,0 +1,7 @@
+Copyright 2025 Phillip Tarrant
+
+Permission is hereby granted, free of charge, to any person obtaining a copy of this software and associated documentation files (the “Software”), to deal in the Software without restriction, including without limitation the rights to use, copy, modify, merge, publish, distribute, sublicense, and/or sell copies of the Software, and to permit persons to whom the Software is furnished to do so, subject to the following conditions:
+
+The above copyright notice and this permission notice shall be included in all copies or substantial portions of the Software.
+
+THE SOFTWARE IS PROVIDED “AS IS”, WITHOUT WARRANTY OF ANY KIND, EXPRESS OR IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY, FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE SOFTWARE.

README.md

@@ -1,793 +1,180 @@
 # SneakyScanner
 
-A comprehensive network scanning and infrastructure monitoring platform with both CLI and web interfaces. SneakyScanner uses masscan for fast port discovery, nmap for service detection, sslyze for SSL/TLS analysis, and Playwright for webpage screenshots to perform comprehensive infrastructure audits.
+A comprehensive network scanning and infrastructure monitoring platform with web interface and CLI scanner. SneakyScanner uses masscan for fast port discovery, nmap for service detection, sslyze for SSL/TLS analysis, and Playwright for webpage screenshots to perform comprehensive infrastructure audits.
 
-**Features:**
-- 🔍 **CLI Scanner** - Standalone scanning tool with YAML-based configuration
-- 🌐 **Web Application** - Flask-based web UI with REST API for scan management
-- 📊 **Database Storage** - SQLite database for scan history and trend analysis
-- ⏱️ **Background Jobs** - Asynchronous scan execution with APScheduler
-- 🔐 **Authentication** - Secure session-based authentication system
-- 📈 **Historical Data** - Track infrastructure changes over time
+**Primary Interface**: Web Application (Flask-based GUI)
+**Scripting/Automation**: REST API (see [API Reference](docs/API_REFERENCE.md))
 
-## Table of Contents
+---
 
-1. [Quick Start](#quick-start)
-   - [Web Application (Recommended)](#web-application-recommended)
-   - [CLI Scanner (Standalone)](#cli-scanner-standalone)
-2. [Features](#features)
-3. [Web Application](#web-application)
-4. [CLI Scanner](#cli-scanner)
-5. [Configuration](#configuration)
-6. [Output Formats](#output-formats)
-7. [API Documentation](#api-documentation)
-8. [Deployment](#deployment)
-9. [Development](#development)
+## Key Features
+
+- 🌐 **Web Dashboard** - Modern web UI for scan management, scheduling, and historical analysis
+- 📊 **Database Storage** - SQLite-based scan history with trend analysis and comparison
+- ⏰ **Scheduled Scans** - Cron-based automated scanning with APScheduler
+- 🔧 **Config Creator** - Web-based target configuration builder for quick setup
+- 🔍 **Network Discovery** - Fast port scanning with masscan (all 65535 ports, TCP/UDP)
+- 🎯 **Service Detection** - Nmap-based service enumeration with version detection
+- 🔒 **SSL/TLS Analysis** - Certificate extraction, TLS version testing, cipher suite analysis
+- 📸 **Screenshot Capture** - Automated webpage screenshots for all discovered web services
+- 📈 **Drift Detection** - Expected vs. actual infrastructure comparison
+- 📋 **Multi-Format Reports** - JSON, HTML, and ZIP archives with visual reports
+- 🔐 **Authentication** - Session-based login for single-user deployments
+- 🔔 **Webhook Alerts** - Real-time notifications via Slack, Discord, PagerDuty, and custom integrations
+- ⚠️ **Alert Rules** - Automated detection of infrastructure misconfigurations and anomalies
 
 ---
 
 ## Quick Start
 
-### Web Application (Recommended)
+### Web Application
 
-The web application provides a complete interface for managing scans, viewing history, and analyzing results.
+**Easy Setup (One Command):**
 
-1. **Configure environment:**
 ```bash
-# Copy example environment file
+# 1. Clone repository
+git clone <repository-url>
+cd SneakyScan
+
+# 2. Run setup script
+./setup.sh
+
+# 3. Access web interface at http://localhost:5000
+```
+
+The setup script will:
+- Generate secure keys automatically
+- Create required directories
+- Build and start the Docker containers
+- Initialize the database on first run
+- Display your login credentials
+
+**Manual Setup (Alternative):**
+
+```bash
+# 1. Clone repository
+git clone <repository-url>
+cd SneakyScan
+
+# 2. Configure environment
 cp .env.example .env
+# Edit .env and set SECRET_KEY, SNEAKYSCANNER_ENCRYPTION_KEY, and INITIAL_PASSWORD
 
-# Generate secure keys (Linux/Mac)
-export SECRET_KEY=$(python3 -c 'import secrets; print(secrets.token_hex(32))')
-export ENCRYPTION_KEY=$(python3 -c 'import secrets; print(secrets.token_urlsafe(32))')
+# 3. Build and start (database auto-initializes on first run)
+docker compose up --build -d
 
-# Update .env file with generated keys
-sed -i "s/your-secret-key-here/$SECRET_KEY/" .env
-sed -i "s/your-encryption-key-here/$ENCRYPTION_KEY/" .env
+# 4. Access web interface
+# Open http://localhost:5000
 ```
 
-2. **Start the web application:**
-```bash
-docker-compose -f docker-compose-web.yml up -d
-```
-
-3. **Access the web interface:**
-- Open http://localhost:5000 in your browser
-- Default password: `admin` (change immediately after first login)
-
-4. **Trigger your first scan:**
-- Click "Run Scan Now" on the dashboard
-- Or use the API:
-```bash
-curl -X POST http://localhost:5000/api/scans \
-  -H "Content-Type: application/json" \
-  -d '{"config_file":"/app/configs/example-site.yaml"}' \
-  -b cookies.txt
-```
-
-See [Deployment Guide](docs/ai/DEPLOYMENT.md) for detailed setup instructions.
-
-### CLI Scanner (Standalone)
-
-For quick one-off scans or scripting, use the standalone CLI scanner:
-
-```bash
-# Build the image
-docker-compose build
-
-# Run a scan
-docker-compose up
-
-# Or run directly
-docker run --rm --privileged --network host \
-  -v $(pwd)/configs:/app/configs:ro \
-  -v $(pwd)/output:/app/output \
-  sneakyscanner /app/configs/example-site.yaml
-```
-
-Results are saved to the `output/` directory as JSON, HTML, and ZIP files.
+**See [Deployment Guide](docs/DEPLOYMENT.md) for detailed setup instructions.**
 
 ---
 
-## Features
+## Documentation
 
-### Web Application (Phase 2)
+### User Guides
+- **[Deployment Guide](docs/DEPLOYMENT.md)** - Installation, configuration, and production deployment
+- **[API Reference](docs/API_REFERENCE.md)** - Complete REST API documentation for scripting and automation
 
-- **Dashboard** - View scan history, statistics, and recent activity
-- **REST API** - Programmatic access to all scan management functions
-- **Background Jobs** - Scans execute asynchronously without blocking
-- **Database Storage** - Complete scan history with queryable data
-- **Authentication** - Secure session-based login system
-- **Pagination** - Efficiently browse large scan datasets
-- **Status Tracking** - Real-time scan progress monitoring
-- **Error Handling** - Comprehensive error logging and reporting
-
-### Network Discovery & Port Scanning
-- **YAML-based configuration** for defining scan targets and expectations
-- **Comprehensive scanning using masscan**:
-  - Ping/ICMP echo detection (masscan --ping)
-  - TCP port scanning (all 65535 ports at 10,000 pps)
-  - UDP port scanning (all 65535 ports at 10,000 pps)
-  - Fast network-wide discovery in seconds
-
-### Service Detection & Enumeration
-- **Service detection using nmap**:
-  - Identifies services running on discovered TCP ports
-  - Extracts product names and versions (e.g., "OpenSSH 8.2p1", "nginx 1.18.0")
-  - Provides detailed service information including extra attributes
-  - Balanced intensity level (5) for accuracy and speed
-
-### Security Assessment
-- **HTTP/HTTPS analysis and SSL/TLS security assessment**:
-  - Detects HTTP vs HTTPS on web services
-  - Extracts SSL certificate details (subject, issuer, expiration, SANs)
-  - Calculates days until certificate expiration for monitoring
-  - Tests TLS version support (TLS 1.0, 1.1, 1.2, 1.3)
-  - Lists all accepted cipher suites for each supported TLS version
-  - Identifies weak cryptographic configurations
-
-### Visual Documentation
-- **Webpage screenshot capture** (NEW):
-  - Automatically captures screenshots of all discovered web services (HTTP/HTTPS)
-  - Uses Playwright with headless Chromium browser
-  - Viewport screenshots (1280x720) for consistent sizing
-  - 15-second timeout per page with graceful error handling
-  - Handles self-signed certificates without errors
-  - Saves screenshots as PNG files with references in JSON reports
-  - Screenshots organized in timestamped directories
-  - Browser reuse for optimal performance
-
-### Reporting & Output
-- **Automatic multi-format output** after each scan:
-  - Machine-readable JSON reports for post-processing
-  - Human-readable HTML reports with dark theme
-  - ZIP archives containing all outputs for easy sharing
-- **HTML report features**:
-  - Comprehensive reports with dark theme for easy reading
-  - Summary dashboard with scan statistics, drift alerts, and security warnings
-  - Site-by-site breakdown with expandable service details
-  - Visual badges for expected vs. unexpected services
-  - SSL/TLS certificate details with expiration warnings
-  - Automatically generated after every scan
-- **Dockerized** for consistent execution environment and root privilege isolation
-- **Expected vs. Actual comparison** to identify infrastructure drift
-- Timestamped reports with complete scan duration metrics
+### Developer Resources
+- **[Roadmap](docs/ROADMAP.md)** - Project roadmap, architecture, and planned features
 
 ---
 
-## Web Application
+## Current Status
 
-### Overview
+**Latest Version**: Phase 5 Complete ✅
+**Last Updated**: 2025-11-19
 
-The SneakyScanner web application provides a Flask-based interface for managing network scans. All scans are stored in a SQLite database, enabling historical analysis and trending.
+### Completed Phases
 
-### Key Features
+- ✅ **Phase 1**: Database schema, SQLAlchemy models, settings system
+- ✅ **Phase 2**: REST API, background jobs, authentication, web UI
+- ✅ **Phase 3**: Dashboard, scheduling, trend charts
+- ✅ **Phase 4**: Config creator, target editor, config management UI
+- ✅ **Phase 5**: Webhooks & alerting, notification templates, alert rules
 
-**Scan Management:**
-- Trigger scans via web UI or REST API
-- View complete scan history with pagination
-- Monitor real-time scan status
-- Delete scans and associated files
+### Next Up: Phase 6 - CLI as API Client
 
-**REST API:**
-- Full CRUD operations for scans
-- Session-based authentication
-- JSON responses for all endpoints
-- Comprehensive error handling
+**Goal**: Create a thin CLI client that calls the Flask API for scan operations, enabling scripting and automation workflows while leveraging centralized database storage and web dashboard features.
 
-**Background Processing:**
-- APScheduler for async scan execution
-- Up to 3 concurrent scans (configurable)
-- Status tracking: `running` → `completed`/`failed`
-- Error capture and logging
+**Planned Features**:
+- API token authentication for CLI access
+- Remote scan triggering and status polling
+- Centralized scan history accessible via web dashboard
+- Scriptable automation workflows
 
-**Database Schema:**
-- 11 normalized tables for scan data
-- Relationships: Scans → Sites → IPs → Ports → Services → Certificates → TLS Versions
-- Efficient queries with indexes
-- SQLite WAL mode for better concurrency
-
-### Web UI Routes
-
-| Route | Description |
-|-------|-------------|
-| `/` | Redirects to dashboard |
-| `/login` | Login page |
-| `/logout` | Logout and destroy session |
-| `/dashboard` | Main dashboard with stats and recent scans |
-| `/scans` | Browse scan history (paginated) |
-| `/scans/<id>` | View detailed scan results |
-
-### API Endpoints
-
-See [API_REFERENCE.md](docs/ai/API_REFERENCE.md) for complete API documentation.
-
-**Core Endpoints:**
-- `POST /api/scans` - Trigger new scan
-- `GET /api/scans` - List scans (paginated, filterable)
-- `GET /api/scans/{id}` - Get scan details
-- `GET /api/scans/{id}/status` - Poll scan status
-- `DELETE /api/scans/{id}` - Delete scan and files
-
-**Settings Endpoints:**
-- `GET /api/settings` - Get all settings
-- `PUT /api/settings/{key}` - Update setting
-- `GET /api/settings/health` - Health check
-
-### Authentication
-
-**Login:**
-```bash
-curl -X POST http://localhost:5000/auth/login \
-  -H "Content-Type: application/json" \
-  -d '{"password":"yourpassword"}' \
-  -c cookies.txt
-```
-
-**Use session for API calls:**
-```bash
-curl -X GET http://localhost:5000/api/scans \
-  -b cookies.txt
-```
-
-**Change password:**
-1. Login to web UI
-2. Navigate to Settings
-3. Update app password
-4. Or use CLI: `python3 web/utils/change_password.py`
+See [Roadmap](docs/ROADMAP.md) for complete feature timeline and future phases.
 
 ---
 
-## CLI Scanner
+## Architecture
 
-### Requirements
-
-- Docker
-- Docker Compose (optional, for easier usage)
-
-### Using Docker Compose
-
-1. Create or modify a configuration file in `configs/`:
-
-```yaml
-title: "My Infrastructure Scan"
-sites:
-  - name: "Web Servers"
-    ips:
-      - address: "192.168.1.10"
-        expected:
-          ping: true
-          tcp_ports: [22, 80, 443]
-          udp_ports: []
+```
+┌─────────────────────────────────────────────────────────────┐
+│                     Flask Web Application                   │
+│  ┌──────────────┐  ┌──────────────┐  ┌──────────────────┐   │
+│  │   Web UI     │  │   REST API   │  │   Scheduler      │   │
+│  │  (Dashboard) │  │ (JSON/CRUD)  │  │  (APScheduler)   │   │
+│  └──────┬───────┘  └──────┬───────┘  └────────┬─────────┘   │
+│         │                 │                    │            │
+│         └─────────────────┴────────────────────┘            │
+│                           │                                 │
+│                  ┌────────▼────────┐                        │
+│                  │   SQLAlchemy    │                        │
+│                  │   (ORM Layer)   │                        │
+│                  └────────┬────────┘                        │
+│                           │                                 │
+│                  ┌────────▼────────┐                        │
+│                  │   SQLite3 DB    │                        │
+│                  │  (scan history) │                        │
+│                  └─────────────────┘                        │
+└───────────────────────────┬─────────────────────────────────┘
+                            │
+                 ┌──────────▼──────────┐
+                 │  Scanner Engine     │
+                 │  (scanner.py)       │
+                 │  ┌────────────────┐ │
+                 │  │ Masscan/Nmap   │ │
+                 │  │ Playwright     │ │
+                 │  │ sslyze         │ │
+                 │  └────────────────┘ │
+                 └─────────────────────┘
 ```
 
-2. Build and run:
-
-```bash
-docker-compose build
-docker-compose up
-```
-
-3. Check results in the `output/` directory:
-   - `scan_report_YYYYMMDD_HHMMSS.json` - JSON report
-   - `scan_report_YYYYMMDD_HHMMSS.html` - HTML report
-   - `scan_report_YYYYMMDD_HHMMSS.zip` - ZIP archive
-   - `scan_report_YYYYMMDD_HHMMSS_screenshots/` - Screenshots directory
-
-## Scan Performance
-
-SneakyScanner uses a five-phase approach for comprehensive scanning:
-
-1. **Ping Scan** (masscan): ICMP echo detection - ~1-2 seconds
-2. **TCP Port Discovery** (masscan): Scans all 65535 TCP ports at 10,000 packets/second - ~13 seconds per 2 IPs
-3. **UDP Port Discovery** (masscan): Scans all 65535 UDP ports at 10,000 packets/second - ~13 seconds per 2 IPs
-4. **Service Detection** (nmap): Identifies services on discovered TCP ports - ~20-60 seconds per IP with open ports
-5. **HTTP/HTTPS Analysis** (Playwright, SSL/TLS): Detects web protocols, captures screenshots, and analyzes certificates - ~10-20 seconds per web service
-
-**Example**: Scanning 2 IPs with 10 open ports each (including 2-3 web services) typically takes 2-3 minutes total.
-
-### Using Docker Directly
-
-1. Build the image:
-
-```bash
-docker build -t sneakyscanner .
-```
-
-2. Run a scan:
-
-```bash
-docker run --rm --privileged --network host \
-  -v $(pwd)/configs:/app/configs:ro \
-  -v $(pwd)/output:/app/output \
-  sneakyscanner /app/configs/your-config.yaml
-```
+**Technology Stack**:
+- **Backend**: Flask 3.x, SQLAlchemy 2.x, SQLite3, APScheduler 3.x
+- **Frontend**: Jinja2, Bootstrap 5, Chart.js, Vanilla JavaScript
+- **Scanner**: Masscan, Nmap, Playwright (Chromium), sslyze
+- **Deployment**: Docker Compose, Gunicorn
 
 ---
 
-## Configuration
-
-The YAML configuration file defines the scan parameters:
-
-```yaml
-title: "Scan Title"  # Required: Report title
-sites:               # Required: List of sites to scan
-  - name: "Site Name"
-    ips:
-      - address: "192.168.1.10"
-        expected:
-          ping: true              # Expected ping response
-          tcp_ports: [22, 80]     # Expected TCP ports
-          udp_ports: [53]         # Expected UDP ports
-```
-
-See `configs/example-site.yaml` for a complete example.
-
----
-
-## Output Formats
-
-After each scan completes, SneakyScanner automatically generates three output formats:
-
-1. **JSON Report** (`scan_report_YYYYMMDD_HHMMSS.json`): Machine-readable scan data with all discovered services, ports, and SSL/TLS information
-2. **HTML Report** (`scan_report_YYYYMMDD_HHMMSS.html`): Human-readable report with dark theme, summary dashboard, and detailed service breakdown
-3. **ZIP Archive** (`scan_report_YYYYMMDD_HHMMSS.zip`): Contains JSON report, HTML report, and all screenshots for easy sharing and archival
-
-All files share the same timestamp for easy correlation. Screenshots are saved in a subdirectory (`scan_report_YYYYMMDD_HHMMSS_screenshots/`) and included in the ZIP archive. The report includes the total scan duration (in seconds) covering all phases: ping scan, TCP/UDP port discovery, service detection, screenshot capture, and report generation.
-
-```json
-{
-  "title": "Sneaky Infra Scan",
-  "scan_time": "2024-01-15T10:30:00Z",
-  "scan_duration": 95.3,
-  "config_file": "/app/configs/example-site.yaml",
-  "sites": [
-    {
-      "name": "Production Web Servers",
-      "ips": [
-        {
-          "address": "192.168.1.10",
-          "expected": {
-            "ping": true,
-            "tcp_ports": [22, 80, 443],
-            "udp_ports": [53]
-          },
-          "actual": {
-            "ping": true,
-            "tcp_ports": [22, 80, 443, 3000],
-            "udp_ports": [53],
-            "services": [
-              {
-                "port": 22,
-                "protocol": "tcp",
-                "service": "ssh",
-                "product": "OpenSSH",
-                "version": "8.2p1"
-              },
-              {
-                "port": 80,
-                "protocol": "tcp",
-                "service": "http",
-                "product": "nginx",
-                "version": "1.18.0",
-                "http_info": {
-                  "protocol": "http",
-                  "screenshot": "scan_report_20250115_103000_screenshots/192_168_1_10_80.png"
-                }
-              },
-              {
-                "port": 443,
-                "protocol": "tcp",
-                "service": "https",
-                "product": "nginx",
-                "http_info": {
-                  "protocol": "https",
-                  "screenshot": "scan_report_20250115_103000_screenshots/192_168_1_10_443.png",
-                  "ssl_tls": {
-                    "certificate": {
-                      "subject": "CN=example.com",
-                      "issuer": "CN=Let's Encrypt Authority X3,O=Let's Encrypt,C=US",
-                      "serial_number": "123456789012345678901234567890",
-                      "not_valid_before": "2025-01-01T00:00:00+00:00",
-                      "not_valid_after": "2025-04-01T23:59:59+00:00",
-                      "days_until_expiry": 89,
-                      "sans": ["example.com", "www.example.com"]
-                    },
-                    "tls_versions": {
-                      "TLS 1.0": {
-                        "supported": false,
-                        "cipher_suites": []
-                      },
-                      "TLS 1.1": {
-                        "supported": false,
-                        "cipher_suites": []
-                      },
-                      "TLS 1.2": {
-                        "supported": true,
-                        "cipher_suites": [
-                          "TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384",
-                          "TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256"
-                        ]
-                      },
-                      "TLS 1.3": {
-                        "supported": true,
-                        "cipher_suites": [
-                          "TLS_AES_256_GCM_SHA384",
-                          "TLS_AES_128_GCM_SHA256"
-                        ]
-                      }
-                    }
-                  }
-                }
-              },
-              {
-                "port": 3000,
-                "protocol": "tcp",
-                "service": "http",
-                "product": "Node.js",
-                "http_info": {
-                  "protocol": "http"
-                }
-              }
-            ]
-          }
-        }
-      ]
-    }
-  ]
-}
-```
-
-## Screenshot Capture Details
-
-SneakyScanner automatically captures webpage screenshots for all discovered HTTP and HTTPS services, providing visual documentation of your infrastructure.
-
-### How It Works
-
-1. **Automatic Detection**: During the HTTP/HTTPS analysis phase, SneakyScanner identifies web services based on:
-   - Nmap service detection results (http, https, ssl, http-proxy)
-   - Common web ports (80, 443, 8000, 8006, 8080, 8081, 8443, 8888, 9443)
-
-2. **Screenshot Capture**: For each web service:
-   - Launches headless Chromium browser (once per scan, reused for all screenshots)
-   - Navigates to the service URL (HTTP or HTTPS)
-   - Waits for network to be idle (up to 15 seconds)
-   - Captures viewport screenshot (1280x720 pixels)
-   - Handles SSL certificate errors gracefully (e.g., self-signed certificates)
-
-3. **Storage**: Screenshots are saved as PNG files:
-   - Directory: `output/scan_report_YYYYMMDD_HHMMSS_screenshots/`
-   - Filename format: `{ip}_{port}.png` (e.g., `192_168_1_10_443.png`)
-   - Referenced in JSON report under `http_info.screenshot`
-
-### Screenshot Configuration
-
-Default settings (configured in `src/screenshot_capture.py`):
-- **Viewport size**: 1280x720 (captures visible area only, not full page)
-- **Timeout**: 15 seconds per page load
-- **Browser**: Chromium (headless mode)
-- **SSL handling**: Ignores HTTPS errors (works with self-signed certificates)
-- **User agent**: Mozilla/5.0 (Windows NT 10.0; Win64; x64)
-
-### Error Handling
-
-Screenshots are captured on a best-effort basis:
-- If a screenshot fails (timeout, connection error, etc.), the scan continues
-- Failed screenshots are logged but don't stop the scan
-- Services without screenshots simply omit the `screenshot` field in JSON output
-
-## HTML Report Generation
-
-SneakyScanner automatically generates comprehensive HTML reports after each scan, providing an easy-to-read visual interface for analyzing scan results.
-
-### Automatic Generation
-
-HTML reports are automatically created after every scan completes, along with JSON reports and ZIP archives. All three outputs share the same timestamp and are saved to the `output/` directory.
-
-### Manual Generation (Optional)
-
-You can also manually generate HTML reports from existing JSON scan data:
-
-```bash
-# Generate HTML report (creates report in same directory as JSON)
-python3 src/report_generator.py output/scan_report_20251113_175235.json
-
-# Specify custom output path
-python3 src/report_generator.py output/scan_report.json /path/to/custom_report.html
-```
-
-### Report Features
-
-The generated HTML report includes:
-
-**Summary Dashboard**:
-- **Scan Statistics**: Total IPs scanned, TCP/UDP ports found, services identified, web services, screenshots captured
-- **Drift Alerts**: Unexpected TCP/UDP ports, missing expected services, new services detected
-- **Security Warnings**: Expiring certificates (<30 days), weak TLS versions (1.0/1.1), self-signed certificates, high port services (>10000)
-
-**Site-by-Site Breakdown**:
-- Organized by logical site grouping from configuration
-- Per-IP sections with status badges (ping, port drift summary)
-- Service tables with expandable details (click any row to expand)
-- Visual badges: green (expected), red (unexpected), yellow (missing/warning)
-
-**Service Details** (click to expand):
-- Product name, version, extra information, OS type
-- HTTP/HTTPS protocol detection
-- Screenshot links for web services
-- SSL/TLS certificate details (expandable):
-  - Subject, issuer, validity dates, serial number
-  - Days until expiration with color-coded warnings
-  - Subject Alternative Names (SANs)
-  - TLS version support (1.0, 1.1, 1.2, 1.3) with cipher suites
-  - Weak TLS and self-signed certificate warnings
-
-**UDP Port Handling**:
-- Expected UDP ports shown with green "Expected" badge
-- Unexpected UDP ports shown with red "Unexpected" badge
-- Missing expected UDP ports shown with yellow "Missing" badge
-- Note: Service detection not available for UDP (nmap limitation)
-
-**Design**:
-- Dark theme with slate/grey color scheme for comfortable reading
-- Responsive layout works on different screen sizes
-- No external dependencies - single HTML file
-- Minimal JavaScript for expand/collapse functionality
-- Optimized hover effects for table rows
-
-### Report Output
-
-The HTML report is a standalone file that can be:
-- Opened directly in any web browser (Chrome, Firefox, Safari, Edge)
-- Shared via email or file transfer
-- Archived for compliance or historical comparison
-- Viewed without an internet connection or web server
-
-Screenshot links in the report are relative paths, so keep the report and screenshot directory together.
-
----
-
-## API Documentation
-
-Complete API reference available at [docs/ai/API_REFERENCE.md](docs/ai/API_REFERENCE.md).
-
-**Quick Reference:**
-
-| Endpoint | Method | Description |
-|----------|--------|-------------|
-| `/api/scans` | POST | Trigger new scan |
-| `/api/scans` | GET | List all scans (paginated) |
-| `/api/scans/{id}` | GET | Get scan details |
-| `/api/scans/{id}/status` | GET | Get scan status |
-| `/api/scans/{id}` | DELETE | Delete scan |
-| `/api/settings` | GET | Get all settings |
-| `/api/settings/{key}` | PUT | Update setting |
-| `/api/settings/health` | GET | Health check |
-
-**Authentication:** All endpoints (except `/api/settings/health`) require session authentication via `/auth/login`.
-
----
-
-## Deployment
-
-### Production Deployment
-
-See [DEPLOYMENT.md](docs/ai/DEPLOYMENT.md) for comprehensive deployment guide.
-
-**Quick Steps:**
-
-1. **Configure environment variables:**
-```bash
-cp .env.example .env
-# Edit .env and set secure keys
-```
-
-2. **Initialize database:**
-```bash
-docker-compose -f docker-compose-web.yml run --rm web python3 init_db.py
-```
-
-3. **Start services:**
-```bash
-docker-compose -f docker-compose-web.yml up -d
-```
-
-4. **Verify health:**
-```bash
-curl http://localhost:5000/api/settings/health
-```
-
-### Docker Volumes
-
-The web application uses persistent volumes:
-
-| Volume | Path | Description |
-|--------|------|-------------|
-| `data` | `/app/data` | SQLite database |
-| `output` | `/app/output` | Scan results (JSON, HTML, ZIP, screenshots) |
-| `logs` | `/app/logs` | Application logs |
-| `configs` | `/app/configs` | YAML scan configurations |
-
-**Backup:**
-```bash
-# Backup database
-docker cp sneakyscanner_web:/app/data/sneakyscanner.db ./backup/
-
-# Backup all scan results
-docker cp sneakyscanner_web:/app/output ./backup/
-
-# Or use docker-compose volumes
-docker run --rm -v sneakyscanner_data:/data -v $(pwd)/backup:/backup alpine tar czf /backup/data.tar.gz /data
-```
-
-### Environment Variables
-
-See `.env.example` for complete configuration options:
-
-**Flask Configuration:**
-- `FLASK_ENV` - Environment mode (production/development)
-- `FLASK_DEBUG` - Debug mode (true/false)
-- `SECRET_KEY` - Flask secret key for sessions (generate with `secrets.token_hex(32)`)
-
-**Database:**
-- `DATABASE_URL` - Database connection string (default: SQLite)
-
-**Security:**
-- `SNEAKYSCANNER_ENCRYPTION_KEY` - Encryption key for sensitive settings (generate with `secrets.token_urlsafe(32)`)
-
-**Scheduler:**
-- `SCHEDULER_EXECUTORS` - Number of concurrent scan workers (default: 2)
-- `SCHEDULER_JOB_DEFAULTS_MAX_INSTANCES` - Max concurrent jobs (default: 3)
-
----
-
-## Development
-
-### Project Structure
-
-```
-SneakyScanner/
-├── src/                     # Scanner engine (CLI)
-│   ├── scanner.py           # Main scanner application
-│   ├── screenshot_capture.py # Webpage screenshot capture
-│   └── report_generator.py  # HTML report generation
-├── web/                     # Web application (Flask)
-│   ├── app.py               # Flask app factory
-│   ├── models.py            # SQLAlchemy models (11 tables)
-│   ├── api/                 # API blueprints
-│   │   ├── scans.py         # Scan management endpoints
-│   │   ├── settings.py      # Settings endpoints
-│   │   └── ...
-│   ├── auth/                # Authentication
-│   │   ├── routes.py        # Login/logout routes
-│   │   ├── decorators.py    # Auth decorators
-│   │   └── models.py        # User model
-│   ├── routes/              # Web UI routes
-│   │   └── main.py          # Dashboard, scans pages
-│   ├── services/            # Business logic
-│   │   ├── scan_service.py  # Scan CRUD operations
-│   │   └── scheduler_service.py # APScheduler integration
-│   ├── jobs/                # Background jobs
-│   │   └── scan_job.py      # Async scan execution
-│   ├── utils/               # Utilities
-│   │   ├── settings.py      # Settings manager
-│   │   ├── pagination.py    # Pagination helper
-│   │   └── validators.py    # Input validation
-│   ├── templates/           # Jinja2 templates
-│   │   ├── base.html        # Base layout
-│   │   ├── login.html       # Login page
-│   │   ├── dashboard.html   # Dashboard
-│   │   └── errors/          # Error templates
-│   └── static/              # Static assets
-│       ├── css/
-│       ├── js/
-│       └── images/
-├── templates/               # Report templates (CLI)
-│   └── report_template.html # HTML report template
-├── tests/                   # Test suite
-│   ├── conftest.py          # Pytest fixtures
-│   ├── test_scan_service.py # Service tests
-│   ├── test_scan_api.py     # API tests
-│   ├── test_authentication.py # Auth tests
-│   ├── test_background_jobs.py # Scheduler tests
-│   └── test_error_handling.py # Error handling tests
-├── migrations/              # Alembic database migrations
-│   └── versions/
-│       ├── 001_initial_schema.py
-│       ├── 002_add_scan_indexes.py
-│       └── 003_add_scan_timing_fields.py
-├── configs/                 # Scan configurations
-│   └── example-site.yaml
-├── output/                  # Scan results
-├── docs/                    # Documentation
-│   ├── ai/                  # Development docs
-│   │   ├── API_REFERENCE.md
-│   │   ├── DEPLOYMENT.md
-│   │   ├── PHASE2.md
-│   │   ├── PHASE2_COMPLETE.md
-│   │   └── ROADMAP.md
-│   └── human/
-├── Dockerfile               # Scanner + web app image
-├── docker-compose.yml       # CLI scanner compose
-├── docker-compose-web.yml   # Web app compose
-├── requirements.txt         # Scanner dependencies
-├── requirements-web.txt     # Web app dependencies
-├── alembic.ini             # Alembic configuration
-├── init_db.py              # Database initialization
-├── .env.example            # Environment template
-├── CLAUDE.md               # Developer guide
-└── README.md               # This file
-```
-
-### Running Tests
-
-**In Docker:**
-```bash
-docker-compose -f docker-compose-web.yml run --rm web pytest tests/ -v
-```
-
-**Locally (requires Python 3.12+):**
-```bash
-pip install -r requirements-web.txt
-pytest tests/ -v
-
-# With coverage
-pytest tests/ --cov=web --cov-report=html
-```
-
-**Test Coverage:**
-- 100 test functions across 6 test files
-- 1,825 lines of test code
-- Coverage: Service layer, API endpoints, authentication, error handling, background jobs
-
-### Database Migrations
-
-**Create new migration:**
-```bash
-docker-compose -f docker-compose-web.yml run --rm web alembic revision --autogenerate -m "Description"
-```
-
-**Apply migrations:**
-```bash
-docker-compose -f docker-compose-web.yml run --rm web alembic upgrade head
-```
-
-**Rollback:**
-```bash
-docker-compose -f docker-compose-web.yml run --rm web alembic downgrade -1
-```
-
 ## Security Notice
 
-This tool requires:
-- `--privileged` flag or `CAP_NET_RAW` capability for masscan and nmap raw socket access
+⚠️ **Important**: This tool requires:
+- `--privileged` flag or `CAP_NET_RAW` capability for raw socket access (masscan/nmap)
 - `--network host` for direct network access
 
-Only use this tool on networks you own or have explicit authorization to scan. Unauthorized network scanning may be illegal in your jurisdiction.
+**Only use this tool on networks you own or have explicit authorization to scan.** Unauthorized network scanning may be illegal in your jurisdiction.
 
----
+### Security Best Practices
 
-## Roadmap
+1. Run on dedicated scan server (not production systems)
+2. Restrict network access with firewall rules
+3. Use strong passwords and encryption keys
+4. Enable HTTPS in production (reverse proxy recommended)
+5. Regularly update Docker images and dependencies
 
-**Current Phase:** Phase 2 Complete ✅
-
-**Completed Phases:**
-- ✅ **Phase 1** - Database foundation, Flask app structure, settings system
-- ✅ **Phase 2** - REST API, background jobs, authentication, basic UI
-
-**Upcoming Phases:**
-- 📋 **Phase 3** - Enhanced dashboard, trend charts, scheduled scans (Weeks 5-6)
-- 📋 **Phase 4** - Email notifications, scan comparison, alert rules (Weeks 7-8)
-- 📋 **Phase 5** - CLI as API client, token authentication (Week 9)
-- 📋 **Phase 6** - Advanced features (vulnerability detection, PDF export, timeline view)
-
-See [ROADMAP.md](docs/ai/ROADMAP.md) for detailed feature planning.
+See [Deployment Guide](docs/DEPLOYMENT.md) for production security checklist.
 
 ---
 
 ## Contributing
 
-This is a personal/small team project. For bugs or feature requests:
+This is a personal project. For bugs or feature requests:
+
 1. Check existing issues
 2. Create detailed bug reports with reproduction steps
 3. Submit pull requests with tests
@@ -800,27 +187,16 @@ MIT License - See LICENSE file for details
 
 ---
 
-## Security Notice
-
-This tool requires:
-- `--privileged` flag or `CAP_NET_RAW` capability for masscan and nmap raw socket access
-- `--network host` for direct network access
-
-**⚠️ Important:** Only use this tool on networks you own or have explicit authorization to scan. Unauthorized network scanning may be illegal in your jurisdiction.
-
----
-
 ## Support
 
-**Documentation:**
-- [API Reference](docs/ai/API_REFERENCE.md)
-- [Deployment Guide](docs/ai/DEPLOYMENT.md)
-- [Developer Guide](CLAUDE.md)
-- [Roadmap](docs/ai/ROADMAP.md)
+**Documentation**:
+- [Deployment Guide](docs/DEPLOYMENT.md)
+- [API Reference](docs/API_REFERENCE.md)
+- [Roadmap](docs/ROADMAP.md)
 
-**Issues:** https://github.com/anthropics/sneakyscanner/issues
+**Issues**: email me ptarrant at gmail dot com
 
 ---
 
-**Version:** 2.0 (Phase 2 Complete)
-**Last Updated:** 2025-11-14
+**Version**: 1.0.0-beta
+**Last Updated**: 2025-11-19

app/docker-entrypoint.sh

@@ -0,0 +1,80 @@
+#!/bin/bash
+set -e
+
+# SneakyScanner Docker Entrypoint Script
+# This script ensures the database is initialized before starting the Flask app
+
+DB_PATH="${DATABASE_URL#sqlite:///}"  # Extract path from sqlite:////app/data/sneakyscanner.db
+DB_DIR=$(dirname "$DB_PATH")
+INIT_MARKER="$DB_DIR/.db_initialized"
+PASSWORD_FILE="/app/logs/admin_password.txt"  # Save to logs dir (mounted, no permission issues)
+
+echo "=== SneakyScanner Startup ==="
+echo "Database path: $DB_PATH"
+echo "Database directory: $DB_DIR"
+
+# Ensure database directory exists
+mkdir -p "$DB_DIR"
+
+# Check if this is the first run (database doesn't exist or not initialized)
+if [ ! -f "$DB_PATH" ] || [ ! -f "$INIT_MARKER" ]; then
+    echo ""
+    echo "=== First Run Detected ==="
+    echo "Initializing database..."
+
+    # Set default password from environment or generate a random one
+    if [ -z "$INITIAL_PASSWORD" ]; then
+        echo "INITIAL_PASSWORD not set, generating random password..."
+        # Generate a 32-character alphanumeric password
+        INITIAL_PASSWORD=$(cat /dev/urandom | tr -dc 'A-Za-z0-9' | head -c 32)
+        # Ensure logs directory exists
+        mkdir -p /app/logs
+        echo "$INITIAL_PASSWORD" > "$PASSWORD_FILE"
+        echo "✓ Random password generated and saved to: ./logs/admin_password.txt"
+        SAVE_PASSWORD_MESSAGE=true
+    fi
+
+    # Run database initialization
+    python3 /app/init_db.py \
+        --db-url "$DATABASE_URL" \
+        --password "$INITIAL_PASSWORD" \
+        --no-migrations \
+        --force
+
+    # Create marker file to indicate successful initialization
+    if [ $? -eq 0 ]; then
+        touch "$INIT_MARKER"
+        echo "✓ Database initialized successfully"
+        echo ""
+        echo "=== IMPORTANT ==="
+        if [ "$SAVE_PASSWORD_MESSAGE" = "true" ]; then
+            echo "Login password saved to: ./logs/admin_password.txt"
+            echo "Password: $INITIAL_PASSWORD"
+        else
+            echo "Login password: $INITIAL_PASSWORD"
+        fi
+        echo "Please change this password after logging in!"
+        echo "=================="
+        echo ""
+    else
+        echo "✗ Database initialization failed!"
+        exit 1
+    fi
+else
+    echo "Database already initialized, skipping init..."
+fi
+
+# Apply any pending migrations (if using migrations in future)
+if [ -f "/app/alembic.ini" ]; then
+    echo "Checking for pending migrations..."
+    # Uncomment when ready to use migrations:
+    # alembic upgrade head
+fi
+
+echo ""
+echo "=== Starting Flask Application ==="
+echo "Flask will be available at http://localhost:5000"
+echo ""
+
+# Execute the main application
+exec "$@"

app/init_db.py

@@ -23,11 +23,112 @@ from alembic import command
 from alembic.config import Config
 from sqlalchemy import create_engine
 from sqlalchemy.orm import sessionmaker
+from datetime import datetime, timezone
 
-from web.models import Base
+from web.models import Base, AlertRule
 from web.utils.settings import PasswordManager, SettingsManager
 
 
+def init_default_alert_rules(session):
+    """
+    Create default alert rules for Phase 5.
+
+    Args:
+        session: Database session
+    """
+    print("Initializing default alert rules...")
+
+    # Check if alert rules already exist
+    existing_rules = session.query(AlertRule).count()
+    if existing_rules > 0:
+        print(f"  Alert rules already exist ({existing_rules} rules), skipping...")
+        return
+
+    default_rules = [
+        {
+            'name': 'Unexpected Port Detection',
+            'rule_type': 'unexpected_port',
+            'enabled': True,
+            'threshold': None,
+            'email_enabled': False,
+            'webhook_enabled': False,
+            'severity': 'warning',
+            'filter_conditions': None,
+            'config_id': None
+        },
+        {
+            'name': 'Drift Detection',
+            'rule_type': 'drift_detection',
+            'enabled': True,
+            'threshold': None,  # No threshold means alert on any drift
+            'email_enabled': False,
+            'webhook_enabled': False,
+            'severity': 'info',
+            'filter_conditions': None,
+            'config_id': None
+        },
+        {
+            'name': 'Certificate Expiry Warning',
+            'rule_type': 'cert_expiry',
+            'enabled': True,
+            'threshold': 30,  # Alert when certs expire in 30 days
+            'email_enabled': False,
+            'webhook_enabled': False,
+            'severity': 'warning',
+            'filter_conditions': None,
+            'config_id': None
+        },
+        {
+            'name': 'Weak TLS Detection',
+            'rule_type': 'weak_tls',
+            'enabled': True,
+            'threshold': None,
+            'email_enabled': False,
+            'webhook_enabled': False,
+            'severity': 'warning',
+            'filter_conditions': None,
+            'config_id': None
+        },
+        {
+            'name': 'Host Down Detection',
+            'rule_type': 'ping_failed',
+            'enabled': True,
+            'threshold': None,
+            'email_enabled': False,
+            'webhook_enabled': False,
+            'severity': 'critical',
+            'filter_conditions': None,
+            'config_id': None
+        }
+    ]
+
+    try:
+        for rule_data in default_rules:
+            rule = AlertRule(
+                name=rule_data['name'],
+                rule_type=rule_data['rule_type'],
+                enabled=rule_data['enabled'],
+                threshold=rule_data['threshold'],
+                email_enabled=rule_data['email_enabled'],
+                webhook_enabled=rule_data['webhook_enabled'],
+                severity=rule_data['severity'],
+                filter_conditions=rule_data['filter_conditions'],
+                config_id=rule_data['config_id'],
+                created_at=datetime.now(timezone.utc),
+                updated_at=datetime.now(timezone.utc)
+            )
+            session.add(rule)
+            print(f"  ✓ Created rule: {rule.name}")
+
+        session.commit()
+        print(f"✓ Created {len(default_rules)} default alert rules")
+
+    except Exception as e:
+        print(f"✗ Failed to create default alert rules: {e}")
+        session.rollback()
+        raise
+
+
 def init_database(db_url: str = "sqlite:///./sneakyscanner.db", run_migrations: bool = True):
     """
     Initialize the database schema and settings.
@@ -78,6 +179,10 @@ def init_database(db_url: str = "sqlite:///./sneakyscanner.db", run_migrations:
         settings_manager = SettingsManager(session)
         settings_manager.init_defaults()
         print("✓ Default settings initialized")
+
+        # Initialize default alert rules
+        init_default_alert_rules(session)
+
     except Exception as e:
         print(f"✗ Failed to initialize settings: {e}")
         session.rollback()
@@ -164,6 +269,9 @@ Examples:
   # Use custom database URL
   python3 init_db.py --db-url postgresql://user:pass@localhost/sneakyscanner
 
+  # Force initialization without prompting (for Docker/scripts)
+  python3 init_db.py --force --password mysecret
+
   # Verify existing database
   python3 init_db.py --verify-only
         """
@@ -192,6 +300,12 @@ Examples:
         help='Create tables directly instead of using migrations'
     )
 
+    parser.add_argument(
+        '--force',
+        action='store_true',
+        help='Force initialization without prompting (for non-interactive environments)'
+    )
+
     args = parser.parse_args()
 
     # Check if database already exists
@@ -200,7 +314,7 @@ Examples:
         db_path = args.db_url.replace('sqlite:///', '')
         db_exists = Path(db_path).exists()
 
-    if db_exists and not args.verify_only:
+    if db_exists and not args.verify_only and not args.force:
         response = input(f"\nDatabase already exists at {db_path}. Reinitialize? (y/N): ")
         if response.lower() != 'y':
             print("Aborting.")

app/migrations/versions/004_add_alert_rule_enhancements.py

@@ -0,0 +1,120 @@
+"""Add enhanced alert features for Phase 5
+
+Revision ID: 004
+Revises: 003
+Create Date: 2025-11-18
+
+"""
+from alembic import op
+import sqlalchemy as sa
+
+
+# revision identifiers, used by Alembic
+revision = '004'
+down_revision = '003'
+branch_labels = None
+depends_on = None
+
+
+def upgrade():
+    """
+    Add enhancements for Phase 5 Alert Rule Engine:
+    - Enhanced alert_rules fields
+    - Enhanced alerts fields
+    - New webhooks table
+    - New webhook_delivery_log table
+    """
+
+    # Enhance alert_rules table
+    with op.batch_alter_table('alert_rules') as batch_op:
+        batch_op.add_column(sa.Column('name', sa.String(255), nullable=True, comment='User-friendly rule name'))
+        batch_op.add_column(sa.Column('webhook_enabled', sa.Boolean(), nullable=False, server_default='0', comment='Whether to send webhooks for this rule'))
+        batch_op.add_column(sa.Column('severity', sa.String(20), nullable=True, comment='Alert severity level (critical, warning, info)'))
+        batch_op.add_column(sa.Column('filter_conditions', sa.Text(), nullable=True, comment='JSON filter conditions for the rule'))
+        batch_op.add_column(sa.Column('config_file', sa.String(255), nullable=True, comment='Optional: specific config file this rule applies to'))
+        batch_op.add_column(sa.Column('updated_at', sa.DateTime(), nullable=True, comment='Last update timestamp'))
+
+    # Enhance alerts table
+    with op.batch_alter_table('alerts') as batch_op:
+        batch_op.add_column(sa.Column('rule_id', sa.Integer(), nullable=True, comment='Associated alert rule'))
+        batch_op.add_column(sa.Column('webhook_sent', sa.Boolean(), nullable=False, server_default='0', comment='Whether webhook was sent'))
+        batch_op.add_column(sa.Column('webhook_sent_at', sa.DateTime(), nullable=True, comment='When webhook was sent'))
+        batch_op.add_column(sa.Column('acknowledged', sa.Boolean(), nullable=False, server_default='0', comment='Whether alert was acknowledged'))
+        batch_op.add_column(sa.Column('acknowledged_at', sa.DateTime(), nullable=True, comment='When alert was acknowledged'))
+        batch_op.add_column(sa.Column('acknowledged_by', sa.String(255), nullable=True, comment='User who acknowledged the alert'))
+        batch_op.create_foreign_key('fk_alerts_rule_id', 'alert_rules', ['rule_id'], ['id'])
+        batch_op.create_index('idx_alerts_rule_id', ['rule_id'])
+        batch_op.create_index('idx_alerts_acknowledged', ['acknowledged'])
+
+    # Create webhooks table
+    op.create_table('webhooks',
+        sa.Column('id', sa.Integer(), nullable=False),
+        sa.Column('name', sa.String(255), nullable=False, comment='Webhook name'),
+        sa.Column('url', sa.Text(), nullable=False, comment='Webhook URL'),
+        sa.Column('enabled', sa.Boolean(), nullable=False, server_default='1', comment='Whether webhook is enabled'),
+        sa.Column('auth_type', sa.String(20), nullable=True, comment='Authentication type: none, bearer, basic, custom'),
+        sa.Column('auth_token', sa.Text(), nullable=True, comment='Encrypted authentication token'),
+        sa.Column('custom_headers', sa.Text(), nullable=True, comment='JSON custom headers'),
+        sa.Column('alert_types', sa.Text(), nullable=True, comment='JSON array of alert types to trigger on'),
+        sa.Column('severity_filter', sa.Text(), nullable=True, comment='JSON array of severities to trigger on'),
+        sa.Column('timeout', sa.Integer(), nullable=True, server_default='10', comment='Request timeout in seconds'),
+        sa.Column('retry_count', sa.Integer(), nullable=True, server_default='3', comment='Number of retry attempts'),
+        sa.Column('created_at', sa.DateTime(), nullable=False),
+        sa.Column('updated_at', sa.DateTime(), nullable=False),
+        sa.PrimaryKeyConstraint('id')
+    )
+
+    # Create webhook_delivery_log table
+    op.create_table('webhook_delivery_log',
+        sa.Column('id', sa.Integer(), nullable=False),
+        sa.Column('webhook_id', sa.Integer(), nullable=False, comment='Associated webhook'),
+        sa.Column('alert_id', sa.Integer(), nullable=False, comment='Associated alert'),
+        sa.Column('status', sa.String(20), nullable=True, comment='Delivery status: success, failed, retrying'),
+        sa.Column('response_code', sa.Integer(), nullable=True, comment='HTTP response code'),
+        sa.Column('response_body', sa.Text(), nullable=True, comment='Response body from webhook'),
+        sa.Column('error_message', sa.Text(), nullable=True, comment='Error message if failed'),
+        sa.Column('attempt_number', sa.Integer(), nullable=True, comment='Which attempt this was'),
+        sa.Column('delivered_at', sa.DateTime(), nullable=False, comment='Delivery timestamp'),
+        sa.ForeignKeyConstraint(['webhook_id'], ['webhooks.id'], ),
+        sa.ForeignKeyConstraint(['alert_id'], ['alerts.id'], ),
+        sa.PrimaryKeyConstraint('id')
+    )
+
+    # Create indexes for webhook_delivery_log
+    op.create_index('idx_webhook_delivery_alert_id', 'webhook_delivery_log', ['alert_id'])
+    op.create_index('idx_webhook_delivery_webhook_id', 'webhook_delivery_log', ['webhook_id'])
+    op.create_index('idx_webhook_delivery_status', 'webhook_delivery_log', ['status'])
+
+
+def downgrade():
+    """Remove Phase 5 alert enhancements."""
+
+    # Drop webhook_delivery_log table and its indexes
+    op.drop_index('idx_webhook_delivery_status', table_name='webhook_delivery_log')
+    op.drop_index('idx_webhook_delivery_webhook_id', table_name='webhook_delivery_log')
+    op.drop_index('idx_webhook_delivery_alert_id', table_name='webhook_delivery_log')
+    op.drop_table('webhook_delivery_log')
+
+    # Drop webhooks table
+    op.drop_table('webhooks')
+
+    # Remove enhancements from alerts table
+    with op.batch_alter_table('alerts') as batch_op:
+        batch_op.drop_index('idx_alerts_acknowledged')
+        batch_op.drop_index('idx_alerts_rule_id')
+        batch_op.drop_constraint('fk_alerts_rule_id', type_='foreignkey')
+        batch_op.drop_column('acknowledged_by')
+        batch_op.drop_column('acknowledged_at')
+        batch_op.drop_column('acknowledged')
+        batch_op.drop_column('webhook_sent_at')
+        batch_op.drop_column('webhook_sent')
+        batch_op.drop_column('rule_id')
+
+    # Remove enhancements from alert_rules table
+    with op.batch_alter_table('alert_rules') as batch_op:
+        batch_op.drop_column('updated_at')
+        batch_op.drop_column('config_file')
+        batch_op.drop_column('filter_conditions')
+        batch_op.drop_column('severity')
+        batch_op.drop_column('webhook_enabled')
+        batch_op.drop_column('name')

app/migrations/versions/005_add_webhook_templates.py

@@ -0,0 +1,83 @@
+"""Add webhook template support
+
+Revision ID: 005
+Revises: 004
+Create Date: 2025-11-18
+
+"""
+from alembic import op
+import sqlalchemy as sa
+import json
+
+
+# revision identifiers, used by Alembic
+revision = '005'
+down_revision = '004'
+branch_labels = None
+depends_on = None
+
+
+# Default template that matches the current JSON payload structure
+DEFAULT_TEMPLATE = """{
+  "event": "alert.created",
+  "alert": {
+    "id": {{ alert.id }},
+    "type": "{{ alert.type }}",
+    "severity": "{{ alert.severity }}",
+    "message": "{{ alert.message }}",
+    {% if alert.ip_address %}"ip_address": "{{ alert.ip_address }}",{% endif %}
+    {% if alert.port %}"port": {{ alert.port }},{% endif %}
+    "acknowledged": {{ alert.acknowledged|lower }},
+    "created_at": "{{ alert.created_at.isoformat() }}"
+  },
+  "scan": {
+    "id": {{ scan.id }},
+    "title": "{{ scan.title }}",
+    "timestamp": "{{ scan.timestamp.isoformat() }}",
+    "status": "{{ scan.status }}"
+  },
+  "rule": {
+    "id": {{ rule.id }},
+    "name": "{{ rule.name }}",
+    "type": "{{ rule.type }}",
+    "threshold": {{ rule.threshold if rule.threshold else 'null' }}
+  }
+}"""
+
+
+def upgrade():
+    """
+    Add webhook template fields:
+    - template: Jinja2 template for payload
+    - template_format: Output format (json, text)
+    - content_type_override: Optional custom Content-Type
+    """
+
+    # Add new columns to webhooks table
+    with op.batch_alter_table('webhooks') as batch_op:
+        batch_op.add_column(sa.Column('template', sa.Text(), nullable=True, comment='Jinja2 template for webhook payload'))
+        batch_op.add_column(sa.Column('template_format', sa.String(20), nullable=True, server_default='json', comment='Template output format: json, text'))
+        batch_op.add_column(sa.Column('content_type_override', sa.String(100), nullable=True, comment='Optional custom Content-Type header'))
+
+    # Populate existing webhooks with default template
+    # This ensures backward compatibility by converting existing webhooks to use the
+    # same JSON structure they're currently sending
+    connection = op.get_bind()
+    connection.execute(
+        sa.text("""
+            UPDATE webhooks
+            SET template = :template,
+                template_format = 'json'
+            WHERE template IS NULL
+        """),
+        {"template": DEFAULT_TEMPLATE}
+    )
+
+
+def downgrade():
+    """Remove webhook template fields."""
+
+    with op.batch_alter_table('webhooks') as batch_op:
+        batch_op.drop_column('content_type_override')
+        batch_op.drop_column('template_format')
+        batch_op.drop_column('template')

app/migrations/versions/006_add_reusable_sites.py

@@ -0,0 +1,161 @@
+"""Add reusable site definitions
+
+Revision ID: 006
+Revises: 005
+Create Date: 2025-11-19
+
+This migration introduces reusable site definitions that can be shared across
+multiple scans. Sites are defined once with CIDR ranges and can be referenced
+in multiple scan configurations.
+"""
+from alembic import op
+import sqlalchemy as sa
+from sqlalchemy import text
+
+
+# revision identifiers, used by Alembic
+revision = '006'
+down_revision = '005'
+branch_labels = None
+depends_on = None
+
+
+def upgrade():
+    """
+    Create new site tables and migrate existing scan_sites data to the new structure.
+    """
+
+    # Create sites table (master site definitions)
+    op.create_table('sites',
+        sa.Column('id', sa.Integer(), autoincrement=True, nullable=False),
+        sa.Column('name', sa.String(length=255), nullable=False, comment='Unique site name'),
+        sa.Column('description', sa.Text(), nullable=True, comment='Site description'),
+        sa.Column('created_at', sa.DateTime(), nullable=False, comment='Site creation time'),
+        sa.Column('updated_at', sa.DateTime(), nullable=False, comment='Last modification time'),
+        sa.PrimaryKeyConstraint('id'),
+        sa.UniqueConstraint('name', name='uix_site_name')
+    )
+    op.create_index(op.f('ix_sites_name'), 'sites', ['name'], unique=True)
+
+    # Create site_cidrs table (CIDR ranges for each site)
+    op.create_table('site_cidrs',
+        sa.Column('id', sa.Integer(), autoincrement=True, nullable=False),
+        sa.Column('site_id', sa.Integer(), nullable=False, comment='FK to sites'),
+        sa.Column('cidr', sa.String(length=45), nullable=False, comment='CIDR notation (e.g., 10.0.0.0/24)'),
+        sa.Column('expected_ping', sa.Boolean(), nullable=True, comment='Expected ping response for this CIDR'),
+        sa.Column('expected_tcp_ports', sa.Text(), nullable=True, comment='JSON array of expected TCP ports'),
+        sa.Column('expected_udp_ports', sa.Text(), nullable=True, comment='JSON array of expected UDP ports'),
+        sa.Column('created_at', sa.DateTime(), nullable=False, comment='CIDR creation time'),
+        sa.ForeignKeyConstraint(['site_id'], ['sites.id'], ),
+        sa.PrimaryKeyConstraint('id'),
+        sa.UniqueConstraint('site_id', 'cidr', name='uix_site_cidr')
+    )
+    op.create_index(op.f('ix_site_cidrs_site_id'), 'site_cidrs', ['site_id'], unique=False)
+
+    # Create site_ips table (IP-level overrides within CIDRs)
+    op.create_table('site_ips',
+        sa.Column('id', sa.Integer(), autoincrement=True, nullable=False),
+        sa.Column('site_cidr_id', sa.Integer(), nullable=False, comment='FK to site_cidrs'),
+        sa.Column('ip_address', sa.String(length=45), nullable=False, comment='IPv4 or IPv6 address'),
+        sa.Column('expected_ping', sa.Boolean(), nullable=True, comment='Override ping expectation for this IP'),
+        sa.Column('expected_tcp_ports', sa.Text(), nullable=True, comment='JSON array of expected TCP ports (overrides CIDR)'),
+        sa.Column('expected_udp_ports', sa.Text(), nullable=True, comment='JSON array of expected UDP ports (overrides CIDR)'),
+        sa.Column('created_at', sa.DateTime(), nullable=False, comment='IP override creation time'),
+        sa.ForeignKeyConstraint(['site_cidr_id'], ['site_cidrs.id'], ),
+        sa.PrimaryKeyConstraint('id'),
+        sa.UniqueConstraint('site_cidr_id', 'ip_address', name='uix_site_cidr_ip')
+    )
+    op.create_index(op.f('ix_site_ips_site_cidr_id'), 'site_ips', ['site_cidr_id'], unique=False)
+
+    # Create scan_site_associations table (many-to-many between scans and sites)
+    op.create_table('scan_site_associations',
+        sa.Column('id', sa.Integer(), autoincrement=True, nullable=False),
+        sa.Column('scan_id', sa.Integer(), nullable=False, comment='FK to scans'),
+        sa.Column('site_id', sa.Integer(), nullable=False, comment='FK to sites'),
+        sa.Column('created_at', sa.DateTime(), nullable=False, comment='Association creation time'),
+        sa.ForeignKeyConstraint(['scan_id'], ['scans.id'], ),
+        sa.ForeignKeyConstraint(['site_id'], ['sites.id'], ),
+        sa.PrimaryKeyConstraint('id'),
+        sa.UniqueConstraint('scan_id', 'site_id', name='uix_scan_site')
+    )
+    op.create_index(op.f('ix_scan_site_associations_scan_id'), 'scan_site_associations', ['scan_id'], unique=False)
+    op.create_index(op.f('ix_scan_site_associations_site_id'), 'scan_site_associations', ['site_id'], unique=False)
+
+    # Migrate existing data
+    connection = op.get_bind()
+
+    # 1. Extract unique site names from existing scan_sites and create master Site records
+    # This groups all historical scan sites by name and creates one master site per unique name
+    connection.execute(text("""
+        INSERT INTO sites (name, description, created_at, updated_at)
+        SELECT DISTINCT
+            site_name,
+            'Migrated from scan_sites' as description,
+            datetime('now') as created_at,
+            datetime('now') as updated_at
+        FROM scan_sites
+        WHERE site_name NOT IN (SELECT name FROM sites)
+    """))
+
+    # 2. Create scan_site_associations linking scans to their sites
+    # This maintains the historical relationship between scans and the sites they used
+    connection.execute(text("""
+        INSERT INTO scan_site_associations (scan_id, site_id, created_at)
+        SELECT DISTINCT
+            ss.scan_id,
+            s.id as site_id,
+            datetime('now') as created_at
+        FROM scan_sites ss
+        INNER JOIN sites s ON s.name = ss.site_name
+        WHERE NOT EXISTS (
+            SELECT 1 FROM scan_site_associations ssa
+            WHERE ssa.scan_id = ss.scan_id AND ssa.site_id = s.id
+        )
+    """))
+
+    # 3. For each migrated site, create a CIDR entry from the IPs in scan_ips
+    # Since historical data has individual IPs, we'll create /32 CIDRs for each unique IP
+    # This preserves the exact IP addresses while fitting them into the new CIDR-based model
+    connection.execute(text("""
+        INSERT INTO site_cidrs (site_id, cidr, expected_ping, expected_tcp_ports, expected_udp_ports, created_at)
+        SELECT DISTINCT
+            s.id as site_id,
+            si.ip_address || '/32' as cidr,
+            si.ping_expected,
+            '[]' as expected_tcp_ports,
+            '[]' as expected_udp_ports,
+            datetime('now') as created_at
+        FROM scan_ips si
+        INNER JOIN scan_sites ss ON ss.id = si.site_id
+        INNER JOIN sites s ON s.name = ss.site_name
+        WHERE NOT EXISTS (
+            SELECT 1 FROM site_cidrs sc
+            WHERE sc.site_id = s.id AND sc.cidr = si.ip_address || '/32'
+        )
+        GROUP BY s.id, si.ip_address, si.ping_expected
+    """))
+
+    print("✓ Migration complete: Reusable sites created from historical scan data")
+    print(f"  - Created {connection.execute(text('SELECT COUNT(*) FROM sites')).scalar()} master site(s)")
+    print(f"  - Created {connection.execute(text('SELECT COUNT(*) FROM site_cidrs')).scalar()} CIDR range(s)")
+    print(f"  - Created {connection.execute(text('SELECT COUNT(*) FROM scan_site_associations')).scalar()} scan-site association(s)")
+
+
+def downgrade():
+    """Remove reusable site tables."""
+
+    # Drop tables in reverse order of creation (respecting foreign keys)
+    op.drop_index(op.f('ix_scan_site_associations_site_id'), table_name='scan_site_associations')
+    op.drop_index(op.f('ix_scan_site_associations_scan_id'), table_name='scan_site_associations')
+    op.drop_table('scan_site_associations')
+
+    op.drop_index(op.f('ix_site_ips_site_cidr_id'), table_name='site_ips')
+    op.drop_table('site_ips')
+
+    op.drop_index(op.f('ix_site_cidrs_site_id'), table_name='site_cidrs')
+    op.drop_table('site_cidrs')
+
+    op.drop_index(op.f('ix_sites_name'), table_name='sites')
+    op.drop_table('sites')
+
+    print("✓ Downgrade complete: Reusable site tables removed")

app/migrations/versions/007_configs_to_database.py

@@ -0,0 +1,102 @@
+"""Add database-stored scan configurations
+
+Revision ID: 007
+Revises: 006
+Create Date: 2025-11-19
+
+This migration introduces database-stored scan configurations to replace YAML
+config files. Configs reference sites from the sites table, enabling visual
+config builder and better data management.
+"""
+from alembic import op
+import sqlalchemy as sa
+from sqlalchemy import text
+
+
+# revision identifiers, used by Alembic
+revision = '007'
+down_revision = '006'
+branch_labels = None
+depends_on = None
+
+
+def upgrade():
+    """
+    Create scan_configs and scan_config_sites tables.
+    Add config_id foreign keys to scans and schedules tables.
+    """
+
+    # Create scan_configs table
+    op.create_table('scan_configs',
+        sa.Column('id', sa.Integer(), autoincrement=True, nullable=False),
+        sa.Column('title', sa.String(length=255), nullable=False, comment='Configuration title'),
+        sa.Column('description', sa.Text(), nullable=True, comment='Configuration description'),
+        sa.Column('created_at', sa.DateTime(), nullable=False, comment='Config creation time'),
+        sa.Column('updated_at', sa.DateTime(), nullable=False, comment='Last modification time'),
+        sa.PrimaryKeyConstraint('id')
+    )
+
+    # Create scan_config_sites table (many-to-many between configs and sites)
+    op.create_table('scan_config_sites',
+        sa.Column('id', sa.Integer(), autoincrement=True, nullable=False),
+        sa.Column('config_id', sa.Integer(), nullable=False, comment='FK to scan_configs'),
+        sa.Column('site_id', sa.Integer(), nullable=False, comment='FK to sites'),
+        sa.Column('created_at', sa.DateTime(), nullable=False, comment='Association creation time'),
+        sa.ForeignKeyConstraint(['config_id'], ['scan_configs.id'], ),
+        sa.ForeignKeyConstraint(['site_id'], ['sites.id'], ),
+        sa.PrimaryKeyConstraint('id'),
+        sa.UniqueConstraint('config_id', 'site_id', name='uix_config_site')
+    )
+    op.create_index(op.f('ix_scan_config_sites_config_id'), 'scan_config_sites', ['config_id'], unique=False)
+    op.create_index(op.f('ix_scan_config_sites_site_id'), 'scan_config_sites', ['site_id'], unique=False)
+
+    # Add config_id to scans table
+    with op.batch_alter_table('scans', schema=None) as batch_op:
+        batch_op.add_column(sa.Column('config_id', sa.Integer(), nullable=True, comment='FK to scan_configs table'))
+        batch_op.create_index('ix_scans_config_id', ['config_id'], unique=False)
+        batch_op.create_foreign_key('fk_scans_config_id', 'scan_configs', ['config_id'], ['id'])
+        # Mark config_file as deprecated in comment (already has nullable=True)
+
+    # Add config_id to schedules table and make config_file nullable
+    with op.batch_alter_table('schedules', schema=None) as batch_op:
+        batch_op.add_column(sa.Column('config_id', sa.Integer(), nullable=True, comment='FK to scan_configs table'))
+        batch_op.create_index('ix_schedules_config_id', ['config_id'], unique=False)
+        batch_op.create_foreign_key('fk_schedules_config_id', 'scan_configs', ['config_id'], ['id'])
+        # Make config_file nullable (it was required before)
+        batch_op.alter_column('config_file', existing_type=sa.Text(), nullable=True)
+
+    connection = op.get_bind()
+
+    print("✓ Migration complete: Scan configs tables created")
+    print("  - Created scan_configs table for database-stored configurations")
+    print("  - Created scan_config_sites association table")
+    print("  - Added config_id to scans table")
+    print("  - Added config_id to schedules table")
+    print("  - Existing YAML configs remain in config_file column for backward compatibility")
+
+
+def downgrade():
+    """Remove scan config tables and columns."""
+
+    # Remove foreign keys and columns from schedules
+    with op.batch_alter_table('schedules', schema=None) as batch_op:
+        batch_op.drop_constraint('fk_schedules_config_id', type_='foreignkey')
+        batch_op.drop_index('ix_schedules_config_id')
+        batch_op.drop_column('config_id')
+        # Restore config_file as required
+        batch_op.alter_column('config_file', existing_type=sa.Text(), nullable=False)
+
+    # Remove foreign keys and columns from scans
+    with op.batch_alter_table('scans', schema=None) as batch_op:
+        batch_op.drop_constraint('fk_scans_config_id', type_='foreignkey')
+        batch_op.drop_index('ix_scans_config_id')
+        batch_op.drop_column('config_id')
+
+    # Drop tables in reverse order
+    op.drop_index(op.f('ix_scan_config_sites_site_id'), table_name='scan_config_sites')
+    op.drop_index(op.f('ix_scan_config_sites_config_id'), table_name='scan_config_sites')
+    op.drop_table('scan_config_sites')
+
+    op.drop_table('scan_configs')
+
+    print("✓ Downgrade complete: Scan config tables and columns removed")

app/migrations/versions/008_expand_cidrs_to_ips.py

@@ -0,0 +1,270 @@
+"""Expand CIDRs to individual IPs with per-IP settings
+
+Revision ID: 008
+Revises: 007
+Create Date: 2025-11-19
+
+This migration changes the site architecture to automatically expand CIDRs into
+individual IPs in the database. Each IP has its own port and ping settings.
+
+Changes:
+- Add site_id to site_ips (direct link to sites, support standalone IPs)
+- Make site_cidr_id nullable (IPs can exist without a CIDR parent)
+- Remove settings from site_cidrs (settings now only at IP level)
+- Add unique constraint: no duplicate IPs within a site
+- Expand existing CIDRs to individual IPs
+"""
+from alembic import op
+import sqlalchemy as sa
+from sqlalchemy import text
+import ipaddress
+
+
+# revision identifiers, used by Alembic
+revision = '008'
+down_revision = '007'
+branch_labels = None
+depends_on = None
+
+
+def upgrade():
+    """
+    Modify schema to support per-IP settings and auto-expand CIDRs.
+    """
+
+    connection = op.get_bind()
+
+    # Check if site_id column already exists
+    inspector = sa.inspect(connection)
+    site_ips_columns = [col['name'] for col in inspector.get_columns('site_ips')]
+    site_cidrs_columns = [col['name'] for col in inspector.get_columns('site_cidrs')]
+
+    # Step 1: Add site_id column to site_ips (will be populated from site_cidr_id)
+    if 'site_id' not in site_ips_columns:
+        print("Adding site_id column to site_ips...")
+        op.add_column('site_ips', sa.Column('site_id', sa.Integer(), nullable=True, comment='FK to sites (direct link)'))
+    else:
+        print("site_id column already exists in site_ips, skipping...")
+
+    # Step 2: Populate site_id from site_cidr_id (before we make it nullable)
+    print("Populating site_id from existing site_cidr relationships...")
+    connection.execute(text("""
+        UPDATE site_ips
+        SET site_id = (
+            SELECT site_id
+            FROM site_cidrs
+            WHERE site_cidrs.id = site_ips.site_cidr_id
+        )
+        WHERE site_cidr_id IS NOT NULL
+    """))
+
+    # Step 3: Make site_id NOT NULL and add foreign key
+    # Check if foreign key exists before creating
+    try:
+        op.alter_column('site_ips', 'site_id', nullable=False)
+        print("Made site_id NOT NULL")
+    except Exception as e:
+        print(f"site_id already NOT NULL or error: {e}")
+
+    # Check if foreign key exists
+    try:
+        op.create_foreign_key('fk_site_ips_site_id', 'site_ips', 'sites', ['site_id'], ['id'])
+        print("Created foreign key fk_site_ips_site_id")
+    except Exception as e:
+        print(f"Foreign key already exists or error: {e}")
+
+    # Check if index exists
+    try:
+        op.create_index(op.f('ix_site_ips_site_id'), 'site_ips', ['site_id'], unique=False)
+        print("Created index ix_site_ips_site_id")
+    except Exception as e:
+        print(f"Index already exists or error: {e}")
+
+    # Step 4: Make site_cidr_id nullable (for standalone IPs)
+    try:
+        op.alter_column('site_ips', 'site_cidr_id', nullable=True)
+        print("Made site_cidr_id nullable")
+    except Exception as e:
+        print(f"site_cidr_id already nullable or error: {e}")
+
+    # Step 5: Drop old unique constraint and create new one (site_id, ip_address)
+    # This prevents duplicate IPs within a site (across all CIDRs and standalone)
+    try:
+        op.drop_constraint('uix_site_cidr_ip', 'site_ips', type_='unique')
+        print("Dropped old constraint uix_site_cidr_ip")
+    except Exception as e:
+        print(f"Constraint already dropped or doesn't exist: {e}")
+
+    try:
+        op.create_unique_constraint('uix_site_ip_address', 'site_ips', ['site_id', 'ip_address'])
+        print("Created new constraint uix_site_ip_address")
+    except Exception as e:
+        print(f"Constraint already exists or error: {e}")
+
+    # Step 6: Expand existing CIDRs to individual IPs
+    print("Expanding existing CIDRs to individual IPs...")
+
+    # Get all existing CIDRs
+    cidrs = connection.execute(text("""
+        SELECT id, site_id, cidr, expected_ping, expected_tcp_ports, expected_udp_ports
+        FROM site_cidrs
+    """)).fetchall()
+
+    expanded_count = 0
+    skipped_count = 0
+
+    for cidr_row in cidrs:
+        cidr_id, site_id, cidr_str, expected_ping, expected_tcp_ports, expected_udp_ports = cidr_row
+
+        try:
+            # Parse CIDR
+            network = ipaddress.ip_network(cidr_str, strict=False)
+
+            # Check size - skip if too large (> /24 for IPv4, > /64 for IPv6)
+            if isinstance(network, ipaddress.IPv4Network) and network.prefixlen < 24:
+                print(f"  ⚠ Skipping large CIDR {cidr_str} (>{network.num_addresses} IPs)")
+                skipped_count += 1
+                continue
+            elif isinstance(network, ipaddress.IPv6Network) and network.prefixlen < 64:
+                print(f"  ⚠ Skipping large CIDR {cidr_str} (>{network.num_addresses} IPs)")
+                skipped_count += 1
+                continue
+
+            # Expand to individual IPs
+            for ip in network.hosts() if network.num_addresses > 2 else [network.network_address]:
+                ip_str = str(ip)
+
+                # Check if this IP already exists (from previous IP overrides)
+                existing = connection.execute(text("""
+                    SELECT id FROM site_ips
+                    WHERE site_cidr_id = :cidr_id AND ip_address = :ip_address
+                """), {'cidr_id': cidr_id, 'ip_address': ip_str}).fetchone()
+
+                if not existing:
+                    # Insert new IP with settings from CIDR
+                    connection.execute(text("""
+                        INSERT INTO site_ips (
+                            site_id, site_cidr_id, ip_address,
+                            expected_ping, expected_tcp_ports, expected_udp_ports,
+                            created_at
+                        )
+                        VALUES (
+                            :site_id, :cidr_id, :ip_address,
+                            :expected_ping, :expected_tcp_ports, :expected_udp_ports,
+                            datetime('now')
+                        )
+                    """), {
+                        'site_id': site_id,
+                        'cidr_id': cidr_id,
+                        'ip_address': ip_str,
+                        'expected_ping': expected_ping,
+                        'expected_tcp_ports': expected_tcp_ports,
+                        'expected_udp_ports': expected_udp_ports
+                    })
+                    expanded_count += 1
+
+        except Exception as e:
+            print(f"  ✗ Error expanding CIDR {cidr_str}: {e}")
+            skipped_count += 1
+            continue
+
+    print(f"  ✓ Expanded {expanded_count} IPs from CIDRs")
+    if skipped_count > 0:
+        print(f"  ⚠ Skipped {skipped_count} CIDRs (too large or errors)")
+
+    # Step 7: Remove settings columns from site_cidrs (now only at IP level)
+    print("Removing settings columns from site_cidrs...")
+    # Re-inspect to get current columns
+    site_cidrs_columns = [col['name'] for col in inspector.get_columns('site_cidrs')]
+
+    if 'expected_ping' in site_cidrs_columns:
+        try:
+            op.drop_column('site_cidrs', 'expected_ping')
+            print("Dropped expected_ping from site_cidrs")
+        except Exception as e:
+            print(f"Error dropping expected_ping: {e}")
+    else:
+        print("expected_ping already dropped from site_cidrs")
+
+    if 'expected_tcp_ports' in site_cidrs_columns:
+        try:
+            op.drop_column('site_cidrs', 'expected_tcp_ports')
+            print("Dropped expected_tcp_ports from site_cidrs")
+        except Exception as e:
+            print(f"Error dropping expected_tcp_ports: {e}")
+    else:
+        print("expected_tcp_ports already dropped from site_cidrs")
+
+    if 'expected_udp_ports' in site_cidrs_columns:
+        try:
+            op.drop_column('site_cidrs', 'expected_udp_ports')
+            print("Dropped expected_udp_ports from site_cidrs")
+        except Exception as e:
+            print(f"Error dropping expected_udp_ports: {e}")
+    else:
+        print("expected_udp_ports already dropped from site_cidrs")
+
+    # Print summary
+    total_sites = connection.execute(text('SELECT COUNT(*) FROM sites')).scalar()
+    total_cidrs = connection.execute(text('SELECT COUNT(*) FROM site_cidrs')).scalar()
+    total_ips = connection.execute(text('SELECT COUNT(*) FROM site_ips')).scalar()
+
+    print("\n✓ Migration 008 complete: CIDRs expanded to individual IPs")
+    print(f"  - Total sites: {total_sites}")
+    print(f"  - Total CIDRs: {total_cidrs}")
+    print(f"  - Total IPs: {total_ips}")
+
+
+def downgrade():
+    """
+    Revert schema changes (restore CIDR-level settings).
+    Note: This will lose per-IP granularity!
+    """
+
+    connection = op.get_bind()
+
+    print("Rolling back to CIDR-level settings...")
+
+    # Step 1: Add settings columns back to site_cidrs
+    op.add_column('site_cidrs', sa.Column('expected_ping', sa.Boolean(), nullable=True))
+    op.add_column('site_cidrs', sa.Column('expected_tcp_ports', sa.Text(), nullable=True))
+    op.add_column('site_cidrs', sa.Column('expected_udp_ports', sa.Text(), nullable=True))
+
+    # Step 2: Populate CIDR settings from first IP in each CIDR (approximation)
+    connection.execute(text("""
+        UPDATE site_cidrs
+        SET
+            expected_ping = (
+                SELECT expected_ping FROM site_ips
+                WHERE site_ips.site_cidr_id = site_cidrs.id
+                LIMIT 1
+            ),
+            expected_tcp_ports = (
+                SELECT expected_tcp_ports FROM site_ips
+                WHERE site_ips.site_cidr_id = site_cidrs.id
+                LIMIT 1
+            ),
+            expected_udp_ports = (
+                SELECT expected_udp_ports FROM site_ips
+                WHERE site_ips.site_cidr_id = site_cidrs.id
+                LIMIT 1
+            )
+    """))
+
+    # Step 3: Delete auto-expanded IPs (keep only original overrides)
+    # In practice, this is difficult to determine, so we'll keep all IPs
+    # and just remove the schema changes
+
+    # Step 4: Drop new unique constraint and restore old one
+    op.drop_constraint('uix_site_ip_address', 'site_ips', type_='unique')
+    op.create_unique_constraint('uix_site_cidr_ip', 'site_ips', ['site_cidr_id', 'ip_address'])
+
+    # Step 5: Make site_cidr_id NOT NULL again
+    op.alter_column('site_ips', 'site_cidr_id', nullable=False)
+
+    # Step 6: Drop site_id column and related constraints
+    op.drop_index(op.f('ix_site_ips_site_id'), table_name='site_ips')
+    op.drop_constraint('fk_site_ips_site_id', 'site_ips', type_='foreignkey')
+    op.drop_column('site_ips', 'site_id')
+
+    print("✓ Downgrade complete: Reverted to CIDR-level settings")

app/migrations/versions/009_remove_cidrs.py

@@ -0,0 +1,210 @@
+"""Remove CIDR table - make sites IP-only
+
+Revision ID: 009
+Revises: 008
+Create Date: 2025-11-19
+
+This migration removes the SiteCIDR table entirely, making sites purely
+IP-based. CIDRs are now only used as a convenience for bulk IP addition,
+not stored as permanent entities.
+
+Changes:
+- Set all site_ips.site_cidr_id to NULL (preserve all IPs)
+- Drop foreign key from site_ips to site_cidrs
+- Drop site_cidrs table
+- Remove site_cidr_id column from site_ips
+
+All existing IPs are preserved. They become "standalone" IPs without
+a CIDR parent.
+"""
+from alembic import op
+import sqlalchemy as sa
+from sqlalchemy import text
+
+
+# revision identifiers, used by Alembic
+revision = '009'
+down_revision = '008'
+branch_labels = None
+depends_on = None
+
+
+def upgrade():
+    """
+    Remove CIDR table and make all IPs standalone.
+    """
+
+    connection = op.get_bind()
+    inspector = sa.inspect(connection)
+
+    print("\n=== Migration 009: Remove CIDR Table ===\n")
+
+    # Get counts before migration
+    try:
+        total_cidrs = connection.execute(text('SELECT COUNT(*) FROM site_cidrs')).scalar()
+        total_ips = connection.execute(text('SELECT COUNT(*) FROM site_ips')).scalar()
+        ips_with_cidr = connection.execute(text(
+            'SELECT COUNT(*) FROM site_ips WHERE site_cidr_id IS NOT NULL'
+        )).scalar()
+
+        print(f"Before migration:")
+        print(f"  - Total CIDRs: {total_cidrs}")
+        print(f"  - Total IPs: {total_ips}")
+        print(f"  - IPs linked to CIDRs: {ips_with_cidr}")
+        print(f"  - Standalone IPs: {total_ips - ips_with_cidr}\n")
+    except Exception as e:
+        print(f"Could not get pre-migration stats: {e}\n")
+
+    # Step 1: Set all site_cidr_id to NULL (preserve all IPs as standalone)
+    print("Step 1: Converting all IPs to standalone (nulling CIDR associations)...")
+    try:
+        result = connection.execute(text("""
+            UPDATE site_ips
+            SET site_cidr_id = NULL
+            WHERE site_cidr_id IS NOT NULL
+        """))
+        print(f"  ✓ Converted {result.rowcount} IPs to standalone\n")
+    except Exception as e:
+        print(f"  ⚠ Error or already done: {e}\n")
+
+    # Step 2: Drop foreign key constraint from site_ips to site_cidrs
+    print("Step 2: Dropping foreign key constraint from site_ips to site_cidrs...")
+    foreign_keys = inspector.get_foreign_keys('site_ips')
+    fk_to_drop = None
+
+    for fk in foreign_keys:
+        if fk['referred_table'] == 'site_cidrs':
+            fk_to_drop = fk['name']
+            break
+
+    if fk_to_drop:
+        try:
+            op.drop_constraint(fk_to_drop, 'site_ips', type_='foreignkey')
+            print(f"  ✓ Dropped foreign key constraint: {fk_to_drop}\n")
+        except Exception as e:
+            print(f"  ⚠ Could not drop foreign key: {e}\n")
+    else:
+        print("  ⚠ Foreign key constraint not found or already dropped\n")
+
+    # Step 3: Drop index on site_cidr_id (if exists)
+    print("Step 3: Dropping index on site_cidr_id...")
+    indexes = inspector.get_indexes('site_ips')
+    index_to_drop = None
+
+    for idx in indexes:
+        if 'site_cidr_id' in idx['column_names']:
+            index_to_drop = idx['name']
+            break
+
+    if index_to_drop:
+        try:
+            op.drop_index(index_to_drop, table_name='site_ips')
+            print(f"  ✓ Dropped index: {index_to_drop}\n")
+        except Exception as e:
+            print(f"  ⚠ Could not drop index: {e}\n")
+    else:
+        print("  ⚠ Index not found or already dropped\n")
+
+    # Step 4: Drop site_cidrs table
+    print("Step 4: Dropping site_cidrs table...")
+    tables = inspector.get_table_names()
+
+    if 'site_cidrs' in tables:
+        try:
+            op.drop_table('site_cidrs')
+            print("  ✓ Dropped site_cidrs table\n")
+        except Exception as e:
+            print(f"  ⚠ Could not drop table: {e}\n")
+    else:
+        print("  ⚠ Table site_cidrs not found or already dropped\n")
+
+    # Step 5: Drop site_cidr_id column from site_ips
+    print("Step 5: Dropping site_cidr_id column from site_ips...")
+    site_ips_columns = [col['name'] for col in inspector.get_columns('site_ips')]
+
+    if 'site_cidr_id' in site_ips_columns:
+        try:
+            op.drop_column('site_ips', 'site_cidr_id')
+            print("  ✓ Dropped site_cidr_id column from site_ips\n")
+        except Exception as e:
+            print(f"  ⚠ Could not drop column: {e}\n")
+    else:
+        print("  ⚠ Column site_cidr_id not found or already dropped\n")
+
+    # Get counts after migration
+    try:
+        final_ips = connection.execute(text('SELECT COUNT(*) FROM site_ips')).scalar()
+        total_sites = connection.execute(text('SELECT COUNT(*) FROM sites')).scalar()
+
+        print("After migration:")
+        print(f"  - Total sites: {total_sites}")
+        print(f"  - Total IPs (all standalone): {final_ips}")
+        print(f"  - CIDRs: N/A (table removed)")
+    except Exception as e:
+        print(f"Could not get post-migration stats: {e}")
+
+    print("\n✓ Migration 009 complete: Sites are now IP-only")
+    print("  All IPs preserved as standalone. CIDRs can still be used")
+    print("  via the API/UI for bulk IP creation, but are not stored.\n")
+
+
+def downgrade():
+    """
+    Recreate site_cidrs table (CANNOT restore original CIDR associations).
+
+    WARNING: This downgrade creates an empty site_cidrs table structure but
+    cannot restore the original CIDR-to-IP associations since that data was
+    deleted. All IPs will remain standalone.
+    """
+
+    connection = op.get_bind()
+
+    print("\n=== Downgrade 009: Recreate CIDR Table Structure ===\n")
+    print("⚠ WARNING: Cannot restore original CIDR associations!")
+    print("  The site_cidrs table structure will be recreated but will be empty.")
+    print("  All IPs will remain standalone. This is a PARTIAL downgrade.\n")
+
+    # Step 1: Recreate site_cidrs table (empty)
+    print("Step 1: Recreating site_cidrs table structure...")
+    try:
+        op.create_table(
+            'site_cidrs',
+            sa.Column('id', sa.Integer(), autoincrement=True, nullable=False),
+            sa.Column('site_id', sa.Integer(), nullable=False),
+            sa.Column('cidr', sa.String(length=45), nullable=False, comment='CIDR notation (e.g., 10.0.0.0/24)'),
+            sa.Column('created_at', sa.DateTime(), nullable=False),
+            sa.PrimaryKeyConstraint('id'),
+            sa.ForeignKeyConstraint(['site_id'], ['sites.id'], ),
+            sa.UniqueConstraint('site_id', 'cidr', name='uix_site_cidr')
+        )
+        print("  ✓ Recreated site_cidrs table (empty)\n")
+    except Exception as e:
+        print(f"  ⚠ Could not create table: {e}\n")
+
+    # Step 2: Add site_cidr_id column back to site_ips (nullable)
+    print("Step 2: Adding site_cidr_id column back to site_ips...")
+    try:
+        op.add_column('site_ips', sa.Column('site_cidr_id', sa.Integer(), nullable=True, comment='FK to site_cidrs (optional, for grouping)'))
+        print("  ✓ Added site_cidr_id column (nullable)\n")
+    except Exception as e:
+        print(f"  ⚠ Could not add column: {e}\n")
+
+    # Step 3: Add foreign key constraint
+    print("Step 3: Adding foreign key constraint...")
+    try:
+        op.create_foreign_key('fk_site_ips_site_cidr_id', 'site_ips', 'site_cidrs', ['site_cidr_id'], ['id'])
+        print("  ✓ Created foreign key constraint\n")
+    except Exception as e:
+        print(f"  ⚠ Could not create foreign key: {e}\n")
+
+    # Step 4: Add index on site_cidr_id
+    print("Step 4: Adding index on site_cidr_id...")
+    try:
+        op.create_index('ix_site_ips_site_cidr_id', 'site_ips', ['site_cidr_id'], unique=False)
+        print("  ✓ Created index on site_cidr_id\n")
+    except Exception as e:
+        print(f"  ⚠ Could not create index: {e}\n")
+
+    print("✓ Downgrade complete: CIDR table structure restored (but empty)")
+    print("  All IPs remain standalone. You would need to manually recreate")
+    print("  CIDR records and associate IPs with them.\n")

app/migrations/versions/010_alert_rules_config_id.py

@@ -0,0 +1,53 @@
+"""Add config_id to alert_rules table
+
+Revision ID: 010
+Revises: 009
+Create Date: 2025-11-19
+
+This migration adds config_id foreign key to alert_rules table to replace
+the config_file column, completing the migration from file-based to
+database-based configurations.
+"""
+from alembic import op
+import sqlalchemy as sa
+
+
+# revision identifiers, used by Alembic
+revision = '010'
+down_revision = '009'
+branch_labels = None
+depends_on = None
+
+
+def upgrade():
+    """
+    Add config_id to alert_rules table and remove config_file.
+    """
+
+    with op.batch_alter_table('alert_rules', schema=None) as batch_op:
+        # Add config_id column with foreign key
+        batch_op.add_column(sa.Column('config_id', sa.Integer(), nullable=True, comment='FK to scan_configs table'))
+        batch_op.create_index('ix_alert_rules_config_id', ['config_id'], unique=False)
+        batch_op.create_foreign_key('fk_alert_rules_config_id', 'scan_configs', ['config_id'], ['id'])
+
+        # Remove the old config_file column
+        batch_op.drop_column('config_file')
+
+    print("✓ Migration complete: AlertRule now uses config_id")
+    print("  - Added config_id foreign key to alert_rules table")
+    print("  - Removed deprecated config_file column")
+
+
+def downgrade():
+    """Remove config_id and restore config_file on alert_rules."""
+
+    with op.batch_alter_table('alert_rules', schema=None) as batch_op:
+        # Remove foreign key and config_id column
+        batch_op.drop_constraint('fk_alert_rules_config_id', type_='foreignkey')
+        batch_op.drop_index('ix_alert_rules_config_id')
+        batch_op.drop_column('config_id')
+
+        # Restore config_file column
+        batch_op.add_column(sa.Column('config_file', sa.String(255), nullable=True, comment='Optional: specific config file this rule applies to'))
+
+    print("✓ Downgrade complete: AlertRule config_id removed, config_file restored")

app/migrations/versions/011_drop_config_file.py

@@ -0,0 +1,86 @@
+"""Drop deprecated config_file columns
+
+Revision ID: 011
+Revises: 010
+Create Date: 2025-11-19
+
+This migration removes the deprecated config_file columns from scans and schedules
+tables. All functionality now uses config_id to reference database-stored configs.
+"""
+from alembic import op
+import sqlalchemy as sa
+
+
+# revision identifiers, used by Alembic
+revision = '011'
+down_revision = '010'
+branch_labels = None
+depends_on = None
+
+
+def upgrade():
+    """
+    Drop config_file columns from scans and schedules tables.
+
+    Prerequisites:
+    - All scans must have config_id set
+    - All schedules must have config_id set
+    - Code must be updated to no longer reference config_file
+    """
+
+    connection = op.get_bind()
+
+    # Check for any records missing config_id
+    result = connection.execute(sa.text(
+        "SELECT COUNT(*) FROM scans WHERE config_id IS NULL"
+    ))
+    scans_without_config = result.scalar()
+
+    result = connection.execute(sa.text(
+        "SELECT COUNT(*) FROM schedules WHERE config_id IS NULL"
+    ))
+    schedules_without_config = result.scalar()
+
+    if scans_without_config > 0:
+        print(f"WARNING: {scans_without_config} scans have NULL config_id")
+        print("  These scans will lose their config reference after migration")
+
+    if schedules_without_config > 0:
+        raise Exception(
+            f"Cannot proceed: {schedules_without_config} schedules have NULL config_id. "
+            "Please set config_id for all schedules before running this migration."
+        )
+
+    # Drop config_file from scans table
+    with op.batch_alter_table('scans', schema=None) as batch_op:
+        batch_op.drop_column('config_file')
+
+    # Drop config_file from schedules table
+    with op.batch_alter_table('schedules', schema=None) as batch_op:
+        batch_op.drop_column('config_file')
+
+    print("✓ Migration complete: Dropped config_file columns")
+    print("  - Removed config_file from scans table")
+    print("  - Removed config_file from schedules table")
+    print("  - All references should now use config_id")
+
+
+def downgrade():
+    """Re-add config_file columns (data will be lost)."""
+
+    # Add config_file back to scans
+    with op.batch_alter_table('scans', schema=None) as batch_op:
+        batch_op.add_column(
+            sa.Column('config_file', sa.Text(), nullable=True,
+                     comment='Path to YAML config used (deprecated)')
+        )
+
+    # Add config_file back to schedules
+    with op.batch_alter_table('schedules', schema=None) as batch_op:
+        batch_op.add_column(
+            sa.Column('config_file', sa.Text(), nullable=True,
+                     comment='Path to YAML config (deprecated)')
+        )
+
+    print("✓ Downgrade complete: Re-added config_file columns")
+    print("  WARNING: config_file values are lost and will be NULL")

app/migrations/versions/012_add_scan_progress.py

@@ -0,0 +1,58 @@
+"""Add scan progress tracking
+
+Revision ID: 012
+Revises: 011
+Create Date: 2024-01-01 00:00:00.000000
+
+"""
+from alembic import op
+import sqlalchemy as sa
+
+
+# revision identifiers, used by Alembic.
+revision = '012'
+down_revision = '011'
+branch_labels = None
+depends_on = None
+
+
+def upgrade():
+    # Add progress tracking columns to scans table
+    op.add_column('scans', sa.Column('current_phase', sa.String(50), nullable=True,
+                  comment='Current scan phase: ping, tcp_scan, udp_scan, service_detection, http_analysis'))
+    op.add_column('scans', sa.Column('total_ips', sa.Integer(), nullable=True,
+                  comment='Total number of IPs to scan'))
+    op.add_column('scans', sa.Column('completed_ips', sa.Integer(), nullable=True, default=0,
+                  comment='Number of IPs completed in current phase'))
+
+    # Create scan_progress table for per-IP progress tracking
+    op.create_table(
+        'scan_progress',
+        sa.Column('id', sa.Integer(), primary_key=True, autoincrement=True),
+        sa.Column('scan_id', sa.Integer(), sa.ForeignKey('scans.id'), nullable=False, index=True),
+        sa.Column('ip_address', sa.String(45), nullable=False, comment='IP address being scanned'),
+        sa.Column('site_name', sa.String(255), nullable=True, comment='Site name this IP belongs to'),
+        sa.Column('phase', sa.String(50), nullable=False,
+                  comment='Phase: ping, tcp_scan, udp_scan, service_detection, http_analysis'),
+        sa.Column('status', sa.String(20), nullable=False, default='pending',
+                  comment='pending, in_progress, completed, failed'),
+        sa.Column('ping_result', sa.Boolean(), nullable=True, comment='Ping response result'),
+        sa.Column('tcp_ports', sa.Text(), nullable=True, comment='JSON array of discovered TCP ports'),
+        sa.Column('udp_ports', sa.Text(), nullable=True, comment='JSON array of discovered UDP ports'),
+        sa.Column('services', sa.Text(), nullable=True, comment='JSON array of detected services'),
+        sa.Column('created_at', sa.DateTime(), nullable=False, server_default=sa.func.now(),
+                  comment='Entry creation time'),
+        sa.Column('updated_at', sa.DateTime(), nullable=False, server_default=sa.func.now(),
+                  onupdate=sa.func.now(), comment='Last update time'),
+        sa.UniqueConstraint('scan_id', 'ip_address', name='uix_scan_progress_ip')
+    )
+
+
+def downgrade():
+    # Drop scan_progress table
+    op.drop_table('scan_progress')
+
+    # Remove progress tracking columns from scans table
+    op.drop_column('scans', 'completed_ips')
+    op.drop_column('scans', 'total_ips')
+    op.drop_column('scans', 'current_phase')

app/requirements-web.txt

@@ -12,7 +12,7 @@ alembic==1.13.0
 # Authentication & Security
 Flask-Login==0.6.3
 bcrypt==4.1.2
-cryptography==41.0.7
+cryptography>=46.0.0
 
 # API & Serialization
 Flask-CORS==4.0.0
@@ -26,6 +26,9 @@ croniter==2.0.1
 # Email Support (Phase 4)
 Flask-Mail==0.9.1
 
+# Webhook Support (Phase 5)
+requests==2.31.0
+
 # Configuration Management
 python-dotenv==1.0.0
 

app/requirements.txt

@@ -1,5 +1,5 @@
 PyYAML==6.0.1
 python-libnmap==0.7.3
-sslyze==6.0.0
+sslyze==6.2.0
 playwright==1.40.0
 Jinja2==3.1.2

app/src/report_generator.py

@@ -78,7 +78,7 @@ class HTMLReportGenerator:
             'title': self.report_data.get('title', 'SneakyScanner Report'),
             'scan_time': self.report_data.get('scan_time'),
             'scan_duration': self.report_data.get('scan_duration'),
-            'config_file': self.report_data.get('config_file'),
+            'config_id': self.report_data.get('config_id'),
             'sites': self.report_data.get('sites', []),
             'summary_stats': summary_stats,
             'drift_alerts': drift_alerts,

app/src/scanner.py

@@ -6,14 +6,17 @@ SneakyScanner - Masscan-based network scanner with YAML configuration
 import argparse
 import json
 import logging
+import os
+import signal
 import subprocess
 import sys
 import tempfile
+import threading
 import time
 import zipfile
 from datetime import datetime
 from pathlib import Path
-from typing import Dict, List, Any
+from typing import Dict, List, Any, Callable, Optional
 import xml.etree.ElementTree as ET
 
 import yaml
@@ -22,24 +25,93 @@ from libnmap.parser import NmapParser
 
 from src.screenshot_capture import ScreenshotCapture
 from src.report_generator import HTMLReportGenerator
+from web.config import NMAP_HOST_TIMEOUT
 
 # Force unbuffered output for Docker
 sys.stdout.reconfigure(line_buffering=True)
 sys.stderr.reconfigure(line_buffering=True)
 
 
-class SneakyScanner:
-    """Wrapper for masscan to perform network scans based on YAML config"""
+class ScanCancelledError(Exception):
+    """Raised when a scan is cancelled by the user."""
+    pass
 
-    def __init__(self, config_path: str, output_dir: str = "/app/output"):
-        self.config_path = Path(config_path)
+
+class SneakyScanner:
+    """Wrapper for masscan to perform network scans based on YAML config or database config"""
+
+    def __init__(self, config_path: str = None, config_id: int = None, config_dict: Dict = None, output_dir: str = "/app/output"):
+        """
+        Initialize scanner with configuration.
+
+        Args:
+            config_path: Path to YAML config file (legacy)
+            config_id: Database config ID (preferred)
+            config_dict: Config dictionary (for direct use)
+            output_dir: Output directory for scan results
+
+        Note: Provide exactly one of config_path, config_id, or config_dict
+        """
+        if sum([config_path is not None, config_id is not None, config_dict is not None]) != 1:
+            raise ValueError("Must provide exactly one of: config_path, config_id, or config_dict")
+
+        self.config_path = Path(config_path) if config_path else None
+        self.config_id = config_id
         self.output_dir = Path(output_dir)
         self.output_dir.mkdir(parents=True, exist_ok=True)
+
+        if config_dict:
+            self.config = config_dict
+            # Process sites: resolve references and expand CIDRs
+            if 'sites' in self.config:
+                self.config['sites'] = self._resolve_sites(self.config['sites'])
+        else:
             self.config = self._load_config()
+
         self.screenshot_capture = None
 
+        # Cancellation support
+        self._cancelled = False
+        self._cancel_lock = threading.Lock()
+        self._active_process = None
+        self._process_lock = threading.Lock()
+
+    def cancel(self):
+        """
+        Cancel the running scan.
+
+        Terminates any active subprocess and sets cancellation flag.
+        """
+        with self._cancel_lock:
+            self._cancelled = True
+
+        with self._process_lock:
+            if self._active_process and self._active_process.poll() is None:
+                try:
+                    # Terminate the process group
+                    os.killpg(os.getpgid(self._active_process.pid), signal.SIGTERM)
+                except (ProcessLookupError, OSError):
+                    pass
+
+    def is_cancelled(self) -> bool:
+        """Check if scan has been cancelled."""
+        with self._cancel_lock:
+            return self._cancelled
+
     def _load_config(self) -> Dict[str, Any]:
-        """Load and validate YAML configuration"""
+        """
+        Load and validate configuration from file or database.
+
+        Supports three formats:
+        1. Legacy: Sites with explicit IP lists
+        2. Site references: Sites referencing database-stored sites
+        3. Inline CIDRs: Sites with CIDR ranges
+        """
+        # Load from database if config_id provided
+        if self.config_id:
+            return self._load_config_from_database(self.config_id)
+
+        # Load from YAML file
         if not self.config_path.exists():
             raise FileNotFoundError(f"Config file not found: {self.config_path}")
 
@@ -51,8 +123,256 @@ class SneakyScanner:
         if not config.get('sites'):
             raise ValueError("Config must include 'sites' field")
 
+        # Process sites: resolve references and expand CIDRs
+        config['sites'] = self._resolve_sites(config['sites'])
+
         return config
 
+    def _load_config_from_database(self, config_id: int) -> Dict[str, Any]:
+        """
+        Load configuration from database by ID.
+
+        Args:
+            config_id: Database config ID
+
+        Returns:
+            Config dictionary with expanded sites
+
+        Raises:
+            ValueError: If config not found or invalid
+        """
+        try:
+            # Import here to avoid circular dependencies and allow scanner to work standalone
+            import os
+            import sys
+
+            # Add parent directory to path for imports
+            sys.path.insert(0, os.path.dirname(os.path.dirname(os.path.abspath(__file__))))
+
+            from sqlalchemy import create_engine
+            from sqlalchemy.orm import sessionmaker
+            from web.models import ScanConfig
+
+            # Create database session
+            db_url = os.environ.get('DATABASE_URL', 'sqlite:////app/data/sneakyscanner.db')
+            engine = create_engine(db_url)
+            Session = sessionmaker(bind=engine)
+            session = Session()
+
+            try:
+                # Load config from database
+                db_config = session.query(ScanConfig).filter_by(id=config_id).first()
+
+                if not db_config:
+                    raise ValueError(f"Config with ID {config_id} not found in database")
+
+                # Build config dict with site references
+                config = {
+                    'title': db_config.title,
+                    'sites': []
+                }
+
+                # Add each site as a site_ref
+                for assoc in db_config.site_associations:
+                    site = assoc.site
+                    config['sites'].append({
+                        'site_ref': site.name
+                    })
+
+                # Process sites: resolve references and expand CIDRs
+                config['sites'] = self._resolve_sites(config['sites'])
+
+                return config
+
+            finally:
+                session.close()
+
+        except ImportError as e:
+            raise ValueError(f"Failed to load config from database (import error): {str(e)}")
+        except Exception as e:
+            raise ValueError(f"Failed to load config from database: {str(e)}")
+
+    def _resolve_sites(self, sites: List[Dict]) -> List[Dict]:
+        """
+        Resolve site references and expand CIDRs to IP lists.
+
+        Converts all site formats into the legacy format (with explicit IPs)
+        for compatibility with the existing scan logic.
+
+        Args:
+            sites: List of site definitions from config
+
+        Returns:
+            List of sites with expanded IP lists
+        """
+        import ipaddress
+
+        resolved_sites = []
+
+        for site_def in sites:
+            # Handle site references
+            if 'site_ref' in site_def:
+                site_ref = site_def['site_ref']
+                # Load site from database
+                site_data = self._load_site_from_database(site_ref)
+                if site_data:
+                    resolved_sites.append(site_data)
+                else:
+                    print(f"WARNING: Site reference '{site_ref}' not found in database", file=sys.stderr)
+                continue
+
+            # Handle inline CIDR definitions
+            if 'cidrs' in site_def:
+                site_name = site_def.get('name', 'Unknown Site')
+                expanded_ips = []
+
+                for cidr_def in site_def['cidrs']:
+                    cidr = cidr_def['cidr']
+                    expected_ping = cidr_def.get('expected_ping', False)
+                    expected_tcp_ports = cidr_def.get('expected_tcp_ports', [])
+                    expected_udp_ports = cidr_def.get('expected_udp_ports', [])
+
+                    # Check if there are IP-level overrides (from database sites)
+                    ip_overrides = cidr_def.get('ip_overrides', [])
+                    override_map = {
+                        override['ip_address']: override
+                        for override in ip_overrides
+                    }
+
+                    # Expand CIDR to IP list
+                    try:
+                        network = ipaddress.ip_network(cidr, strict=False)
+                        ip_list = [str(ip) for ip in network.hosts()]
+
+                        # If network has only 1 address (like /32), hosts() returns empty
+                        if not ip_list:
+                            ip_list = [str(network.network_address)]
+
+                        # Create IP config for each IP in the CIDR
+                        for ip_address in ip_list:
+                            # Check if this IP has an override
+                            if ip_address in override_map:
+                                override = override_map[ip_address]
+                                ip_config = {
+                                    'address': ip_address,
+                                    'expected': {
+                                        'ping': override.get('expected_ping', expected_ping),
+                                        'tcp_ports': override.get('expected_tcp_ports', expected_tcp_ports),
+                                        'udp_ports': override.get('expected_udp_ports', expected_udp_ports)
+                                    }
+                                }
+                            else:
+                                # Use CIDR-level defaults
+                                ip_config = {
+                                    'address': ip_address,
+                                    'expected': {
+                                        'ping': expected_ping,
+                                        'tcp_ports': expected_tcp_ports,
+                                        'udp_ports': expected_udp_ports
+                                    }
+                                }
+
+                            expanded_ips.append(ip_config)
+
+                    except ValueError as e:
+                        print(f"WARNING: Invalid CIDR '{cidr}': {e}", file=sys.stderr)
+                        continue
+
+                # Add expanded site
+                resolved_sites.append({
+                    'name': site_name,
+                    'ips': expanded_ips
+                })
+                continue
+
+            # Legacy format: already has 'ips' list
+            if 'ips' in site_def:
+                resolved_sites.append(site_def)
+                continue
+
+            print(f"WARNING: Site definition missing required fields: {site_def}", file=sys.stderr)
+
+        return resolved_sites
+
+    def _load_site_from_database(self, site_name: str) -> Dict[str, Any]:
+        """
+        Load a site definition from the database.
+
+        IPs are pre-expanded in the database, so we just load them directly.
+
+        Args:
+            site_name: Name of the site to load
+
+        Returns:
+            Site definition dict with IPs, or None if not found
+        """
+        try:
+            # Import database modules
+            import os
+            import sys
+
+            # Add parent directory to path if needed
+            parent_dir = str(Path(__file__).parent.parent)
+            if parent_dir not in sys.path:
+                sys.path.insert(0, parent_dir)
+
+            from sqlalchemy import create_engine
+            from sqlalchemy.orm import sessionmaker, joinedload
+            from web.models import Site
+
+            # Get database URL from environment
+            database_url = os.environ.get('DATABASE_URL', 'sqlite:///./sneakyscanner.db')
+
+            # Create engine and session
+            engine = create_engine(database_url)
+            Session = sessionmaker(bind=engine)
+            session = Session()
+
+            # Query site with all IPs (CIDRs are already expanded)
+            site = (
+                session.query(Site)
+                .options(joinedload(Site.ips))
+                .filter(Site.name == site_name)
+                .first()
+            )
+
+            if not site:
+                session.close()
+                return None
+
+            # Load all IPs directly from database (already expanded)
+            expanded_ips = []
+
+            for ip_obj in site.ips:
+                # Get settings from IP (no need to merge with CIDR defaults)
+                expected_ping = ip_obj.expected_ping if ip_obj.expected_ping is not None else False
+                expected_tcp_ports = json.loads(ip_obj.expected_tcp_ports) if ip_obj.expected_tcp_ports else []
+                expected_udp_ports = json.loads(ip_obj.expected_udp_ports) if ip_obj.expected_udp_ports else []
+
+                ip_config = {
+                    'address': ip_obj.ip_address,
+                    'expected': {
+                        'ping': expected_ping,
+                        'tcp_ports': expected_tcp_ports,
+                        'udp_ports': expected_udp_ports
+                    }
+                }
+
+                expanded_ips.append(ip_config)
+
+            session.close()
+
+            return {
+                'name': site.name,
+                'ips': expanded_ips
+            }
+
+        except Exception as e:
+            print(f"ERROR: Failed to load site '{site_name}' from database: {e}", file=sys.stderr)
+            import traceback
+            traceback.print_exc()
+            return None
+
     def _run_masscan(self, targets: List[str], ports: str, protocol: str) -> List[Dict]:
         """
         Run masscan and return parsed results
@@ -98,11 +418,31 @@ class SneakyScanner:
                 raise ValueError(f"Invalid protocol: {protocol}")
 
             print(f"Running: {' '.join(cmd)}", flush=True)
-            result = subprocess.run(cmd, capture_output=True, text=True)
+
+            # Use Popen for cancellation support
+            with self._process_lock:
+                self._active_process = subprocess.Popen(
+                    cmd,
+                    stdout=subprocess.PIPE,
+                    stderr=subprocess.PIPE,
+                    text=True,
+                    start_new_session=True
+                )
+
+            stdout, stderr = self._active_process.communicate()
+            returncode = self._active_process.returncode
+
+            with self._process_lock:
+                self._active_process = None
+
+            # Check if cancelled
+            if self.is_cancelled():
+                return []
+
             print(f"Masscan {protocol.upper()} scan completed", flush=True)
 
-            if result.returncode != 0:
-                print(f"Masscan stderr: {result.stderr}", file=sys.stderr)
+            if returncode != 0:
+                print(f"Masscan stderr: {stderr}", file=sys.stderr)
 
             # Parse masscan JSON output
             results = []
@@ -150,11 +490,31 @@ class SneakyScanner:
             ]
 
             print(f"Running: {' '.join(cmd)}", flush=True)
-            result = subprocess.run(cmd, capture_output=True, text=True)
+
+            # Use Popen for cancellation support
+            with self._process_lock:
+                self._active_process = subprocess.Popen(
+                    cmd,
+                    stdout=subprocess.PIPE,
+                    stderr=subprocess.PIPE,
+                    text=True,
+                    start_new_session=True
+                )
+
+            stdout, stderr = self._active_process.communicate()
+            returncode = self._active_process.returncode
+
+            with self._process_lock:
+                self._active_process = None
+
+            # Check if cancelled
+            if self.is_cancelled():
+                return {}
+
             print(f"Masscan PING scan completed", flush=True)
 
-            if result.returncode != 0:
-                print(f"Masscan stderr: {result.stderr}", file=sys.stderr, flush=True)
+            if returncode != 0:
+                print(f"Masscan stderr: {stderr}", file=sys.stderr, flush=True)
 
             # Parse results
             responding_ips = set()
@@ -192,6 +552,10 @@ class SneakyScanner:
         all_services = {}
 
         for ip, ports in ip_ports.items():
+            # Check if cancelled before each host
+            if self.is_cancelled():
+                break
+
             if not ports:
                 all_services[ip] = []
                 continue
@@ -213,14 +577,33 @@ class SneakyScanner:
                     '--version-intensity', '5',  # Balanced speed/accuracy
                     '-p', port_list,
                     '-oX', xml_output,  # XML output
-                    '--host-timeout', '5m',  # Timeout per host
+                    '--host-timeout', NMAP_HOST_TIMEOUT,  # Timeout per host
                     ip
                 ]
 
-                result = subprocess.run(cmd, capture_output=True, text=True, timeout=600)
+                # Use Popen for cancellation support
+                with self._process_lock:
+                    self._active_process = subprocess.Popen(
+                        cmd,
+                        stdout=subprocess.PIPE,
+                        stderr=subprocess.PIPE,
+                        text=True,
+                        start_new_session=True
+                    )
 
-                if result.returncode != 0:
-                    print(f"  Nmap warning for {ip}: {result.stderr}", file=sys.stderr, flush=True)
+                stdout, stderr = self._active_process.communicate(timeout=600)
+                returncode = self._active_process.returncode
+
+                with self._process_lock:
+                    self._active_process = None
+
+                # Check if cancelled
+                if self.is_cancelled():
+                    Path(xml_output).unlink(missing_ok=True)
+                    break
+
+                if returncode != 0:
+                    print(f"  Nmap warning for {ip}: {stderr}", file=sys.stderr, flush=True)
 
                 # Parse XML output
                 services = self._parse_nmap_xml(xml_output)
@@ -293,29 +676,57 @@ class SneakyScanner:
 
         return services
 
-    def _is_likely_web_service(self, service: Dict) -> bool:
+    def _is_likely_web_service(self, service: Dict, ip: str = None) -> bool:
         """
-        Check if a service is likely HTTP/HTTPS based on nmap detection or common web ports
+        Check if a service is a web server by actually making an HTTP request
 
         Args:
             service: Service dictionary from nmap results
+            ip: IP address to test (required for HTTP probe)
 
         Returns:
-            True if service appears to be web-related
+            True if service responds to HTTP/HTTPS requests
         """
-        # Check service name
+        import requests
+        import urllib3
+        urllib3.disable_warnings(urllib3.exceptions.InsecureRequestWarning)
+
+        # Quick check for known web service names first
         web_services = ['http', 'https', 'ssl', 'http-proxy', 'https-alt',
                        'http-alt', 'ssl/http', 'ssl/https']
         service_name = service.get('service', '').lower()
 
+        # If no IP provided, can't do HTTP probe
+        port = service.get('port')
+        if not ip or not port:
+            # check just the service if no IP - honestly shouldn't get here, but just incase...
             if service_name in web_services:
                 return True
+            return False
 
-        # Check common non-standard web ports
-        web_ports = [80, 443, 8000, 8006, 8008, 8080, 8081, 8443, 8888, 9443]
-        port = service.get('port')
+        # Actually try to connect - this is the definitive test
+        # Try HTTPS first, then HTTP
+        for protocol in ['https', 'http']:
+            url = f"{protocol}://{ip}:{port}/"
+            try:
+                response = requests.get(
+                    url,
+                    timeout=3,
+                    verify=False,
+                    allow_redirects=False
+                )
+                # Any status code means it's a web server
+                # (including 404, 500, etc. - still a web server)
+                return True
+            except requests.exceptions.SSLError:
+                # SSL error on HTTPS, try HTTP next
+                continue
+            except (requests.exceptions.ConnectionError,
+                    requests.exceptions.Timeout,
+                    requests.exceptions.RequestException):
+                continue
 
-        return port in web_ports
+        return False
 
     def _detect_http_https(self, ip: str, port: int, timeout: int = 5) -> str:
         """
@@ -503,7 +914,7 @@ class SneakyScanner:
             ip_results = {}
 
             for service in services:
-                if not self._is_likely_web_service(service):
+                if not self._is_likely_web_service(service, ip):
                     continue
 
                 port = service['port']
@@ -549,14 +960,24 @@ class SneakyScanner:
 
         return all_results
 
-    def scan(self) -> Dict[str, Any]:
+    def scan(self, progress_callback: Optional[Callable] = None) -> Dict[str, Any]:
         """
         Perform complete scan based on configuration
 
+        Args:
+            progress_callback: Optional callback function for progress updates.
+                              Called with (phase, ip, data) where:
+                              - phase: 'init', 'ping', 'tcp_scan', 'udp_scan', 'service_detection', 'http_analysis'
+                              - ip: IP address being processed (or None for phase start)
+                              - data: Dict with progress data (results, counts, etc.)
+
         Returns:
             Dictionary containing scan results
         """
         print(f"Starting scan: {self.config['title']}", flush=True)
+        if self.config_id:
+            print(f"Config ID: {self.config_id}", flush=True)
+        elif self.config_path:
             print(f"Config: {self.config_path}", flush=True)
 
         # Record start time
@@ -586,17 +1007,61 @@ class SneakyScanner:
         all_ips = sorted(list(all_ips))
         print(f"Total IPs to scan: {len(all_ips)}", flush=True)
 
+        # Report initialization with total IP count
+        if progress_callback:
+            progress_callback('init', None, {
+                'total_ips': len(all_ips),
+                'ip_to_site': ip_to_site
+            })
+
         # Perform ping scan
         print(f"\n[1/5] Performing ping scan on {len(all_ips)} IPs...", flush=True)
+        if progress_callback:
+            progress_callback('ping', None, {'status': 'starting'})
         ping_results = self._run_ping_scan(all_ips)
 
+        # Check for cancellation
+        if self.is_cancelled():
+            print("\nScan cancelled by user", flush=True)
+            raise ScanCancelledError("Scan cancelled by user")
+
+        # Report ping results
+        if progress_callback:
+            progress_callback('ping', None, {
+                'status': 'completed',
+                'results': ping_results
+            })
+
         # Perform TCP scan (all ports)
         print(f"\n[2/5] Performing TCP scan on {len(all_ips)} IPs (ports 0-65535)...", flush=True)
+        if progress_callback:
+            progress_callback('tcp_scan', None, {'status': 'starting'})
         tcp_results = self._run_masscan(all_ips, '0-65535', 'tcp')
 
-        # Perform UDP scan (all ports)
-        print(f"\n[3/5] Performing UDP scan on {len(all_ips)} IPs (ports 0-65535)...", flush=True)
-        udp_results = self._run_masscan(all_ips, '0-65535', 'udp')
+        # Check for cancellation
+        if self.is_cancelled():
+            print("\nScan cancelled by user", flush=True)
+            raise ScanCancelledError("Scan cancelled by user")
+
+        # Perform UDP scan (if enabled)
+        udp_enabled = os.environ.get('UDP_SCAN_ENABLED', 'false').lower() == 'true'
+        udp_ports = os.environ.get('UDP_PORTS', '53,67,68,69,123,161,500,514,1900')
+
+        if udp_enabled:
+            print(f"\n[3/5] Performing UDP scan on {len(all_ips)} IPs (ports {udp_ports})...", flush=True)
+            if progress_callback:
+                progress_callback('udp_scan', None, {'status': 'starting'})
+            udp_results = self._run_masscan(all_ips, udp_ports, 'udp')
+
+            # Check for cancellation
+            if self.is_cancelled():
+                print("\nScan cancelled by user", flush=True)
+                raise ScanCancelledError("Scan cancelled by user")
+        else:
+            print(f"\n[3/5] Skipping UDP scan (disabled)...", flush=True)
+            if progress_callback:
+                progress_callback('udp_scan', None, {'status': 'skipped'})
+            udp_results = []
 
         # Organize results by IP
         results_by_ip = {}
@@ -631,20 +1096,56 @@ class SneakyScanner:
             results_by_ip[ip]['actual']['tcp_ports'].sort()
             results_by_ip[ip]['actual']['udp_ports'].sort()
 
+        # Report TCP/UDP scan results with discovered ports per IP
+        if progress_callback:
+            tcp_udp_results = {}
+            for ip in all_ips:
+                tcp_udp_results[ip] = {
+                    'tcp_ports': results_by_ip[ip]['actual']['tcp_ports'],
+                    'udp_ports': results_by_ip[ip]['actual']['udp_ports']
+                }
+            progress_callback('tcp_scan', None, {
+                'status': 'completed',
+                'results': tcp_udp_results
+            })
+
         # Perform service detection on TCP ports
         print(f"\n[4/5] Performing service detection on discovered TCP ports...", flush=True)
+        if progress_callback:
+            progress_callback('service_detection', None, {'status': 'starting'})
         ip_ports = {ip: results_by_ip[ip]['actual']['tcp_ports'] for ip in all_ips}
         service_results = self._run_nmap_service_detection(ip_ports)
 
+        # Check for cancellation
+        if self.is_cancelled():
+            print("\nScan cancelled by user", flush=True)
+            raise ScanCancelledError("Scan cancelled by user")
+
         # Add service information to results
         for ip, services in service_results.items():
             if ip in results_by_ip:
                 results_by_ip[ip]['actual']['services'] = services
 
+        # Report service detection results
+        if progress_callback:
+            progress_callback('service_detection', None, {
+                'status': 'completed',
+                'results': service_results
+            })
+
         # Perform HTTP/HTTPS analysis on web services
         print(f"\n[5/5] Analyzing HTTP/HTTPS services and SSL/TLS configuration...", flush=True)
+        if progress_callback:
+            progress_callback('http_analysis', None, {'status': 'starting'})
         http_results = self._run_http_analysis(service_results)
 
+        # Report HTTP analysis completion
+        if progress_callback:
+            progress_callback('http_analysis', None, {
+                'status': 'completed',
+                'results': http_results
+            })
+
         # Merge HTTP analysis into service results
         for ip, port_results in http_results.items():
             if ip in results_by_ip:
@@ -662,7 +1163,7 @@ class SneakyScanner:
             'title': self.config['title'],
             'scan_time': datetime.utcnow().isoformat() + 'Z',
             'scan_duration': scan_duration,
-            'config_file': str(self.config_path),
+            'config_id': self.config_id,
             'sites': []
         }
 
@@ -768,6 +1269,8 @@ class SneakyScanner:
                             # Preserve directory structure in ZIP
                             arcname = f"{screenshot_dir.name}/{screenshot_file.name}"
                             zipf.write(screenshot_file, arcname)
+                    # Track screenshot directory for database storage
+                    output_paths['screenshots'] = screenshot_dir
 
             output_paths['zip'] = zip_path
             print(f"ZIP archive saved to: {zip_path}", flush=True)

app/templates/report_template.html

@@ -490,8 +490,8 @@
             <div class="header-meta">
                 <span>📅 <strong>Scan Time:</strong> {{ scan_time | format_date }}</span>
                 <span>⏱️ <strong>Duration:</strong> {{ scan_duration | format_duration }}</span>
-                {% if config_file %}
-                <span>📄 <strong>Config:</strong> {{ config_file }}</span>
+                {% if config_id %}
+                <span>📄 <strong>Config ID:</strong> {{ config_id }}</span>
                 {% endif %}
             </div>
         </div>

app/tests/conftest.py

@@ -13,7 +13,7 @@ from sqlalchemy import create_engine
 from sqlalchemy.orm import sessionmaker
 
 from web.app import create_app
-from web.models import Base, Scan
+from web.models import Base, Scan, ScanConfig
 from web.utils.settings import PasswordManager, SettingsManager
 
 
@@ -53,7 +53,7 @@ def sample_scan_report():
         'title': 'Test Scan',
         'scan_time': '2025-11-14T10:30:00Z',
         'scan_duration': 125.5,
-        'config_file': '/app/configs/test.yaml',
+        'config_id': 1,
         'sites': [
             {
                 'name': 'Test Site',
@@ -199,6 +199,53 @@ def sample_invalid_config_file(tmp_path):
     return str(config_file)
 
 
+@pytest.fixture
+def sample_db_config(db):
+    """
+    Create a sample database config for testing.
+
+    Args:
+        db: Database session fixture
+
+    Returns:
+        ScanConfig model instance with ID
+    """
+    import json
+
+    config_data = {
+        'title': 'Test Scan',
+        'sites': [
+            {
+                'name': 'Test Site',
+                'ips': [
+                    {
+                        'address': '192.168.1.10',
+                        'expected': {
+                            'ping': True,
+                            'tcp_ports': [22, 80, 443],
+                            'udp_ports': [53],
+                            'services': ['ssh', 'http', 'https']
+                        }
+                    }
+                ]
+            }
+        ]
+    }
+
+    scan_config = ScanConfig(
+        title='Test Scan',
+        config_data=json.dumps(config_data),
+        created_at=datetime.utcnow(),
+        updated_at=datetime.utcnow()
+    )
+
+    db.add(scan_config)
+    db.commit()
+    db.refresh(scan_config)
+
+    return scan_config
+
+
 @pytest.fixture(scope='function')
 def app():
     """
@@ -269,7 +316,7 @@ def sample_scan(db):
     scan = Scan(
         timestamp=datetime.utcnow(),
         status='completed',
-        config_file='/app/configs/test.yaml',
+        config_id=1,
         title='Test Scan',
         duration=125.5,
         triggered_by='test',

app/tests/test_background_jobs.py

@@ -23,12 +23,12 @@ class TestBackgroundJobs:
         assert app.scheduler.scheduler is not None
         assert app.scheduler.scheduler.running
 
-    def test_queue_scan_job(self, app, db, sample_config_file):
+    def test_queue_scan_job(self, app, db, sample_db_config):
         """Test queuing a scan for background execution."""
         # Create a scan via service
         scan_service = ScanService(db)
         scan_id = scan_service.trigger_scan(
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             triggered_by='test',
             scheduler=app.scheduler
         )
@@ -43,12 +43,12 @@ class TestBackgroundJobs:
         assert job is not None
         assert job.id == f'scan_{scan_id}'
 
-    def test_trigger_scan_without_scheduler(self, db, sample_config_file):
+    def test_trigger_scan_without_scheduler(self, db, sample_db_config):
         """Test triggering scan without scheduler logs warning."""
         # Create scan without scheduler
         scan_service = ScanService(db)
         scan_id = scan_service.trigger_scan(
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             triggered_by='test',
             scheduler=None  # No scheduler
         )
@@ -58,13 +58,13 @@ class TestBackgroundJobs:
         assert scan is not None
         assert scan.status == 'running'
 
-    def test_scheduler_service_queue_scan(self, app, db, sample_config_file):
+    def test_scheduler_service_queue_scan(self, app, db, sample_db_config):
         """Test SchedulerService.queue_scan directly."""
         # Create scan record first
         scan = Scan(
             timestamp=datetime.utcnow(),
             status='running',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             title='Test Scan',
             triggered_by='test'
         )
@@ -72,27 +72,27 @@ class TestBackgroundJobs:
         db.commit()
 
         # Queue the scan
-        job_id = app.scheduler.queue_scan(scan.id, sample_config_file)
+        job_id = app.scheduler.queue_scan(scan.id, sample_db_config)
 
         # Verify job was queued
         assert job_id == f'scan_{scan.id}'
         job = app.scheduler.scheduler.get_job(job_id)
         assert job is not None
 
-    def test_scheduler_list_jobs(self, app, db, sample_config_file):
+    def test_scheduler_list_jobs(self, app, db, sample_db_config):
         """Test listing scheduled jobs."""
         # Queue a few scans
         for i in range(3):
             scan = Scan(
                 timestamp=datetime.utcnow(),
                 status='running',
-                config_file=sample_config_file,
+                config_id=sample_db_config.id,
                 title=f'Test Scan {i}',
                 triggered_by='test'
             )
             db.add(scan)
             db.commit()
-            app.scheduler.queue_scan(scan.id, sample_config_file)
+            app.scheduler.queue_scan(scan.id, sample_db_config)
 
         # List jobs
         jobs = app.scheduler.list_jobs()
@@ -106,20 +106,20 @@ class TestBackgroundJobs:
             assert 'name' in job
             assert 'trigger' in job
 
-    def test_scheduler_get_job_status(self, app, db, sample_config_file):
+    def test_scheduler_get_job_status(self, app, db, sample_db_config):
         """Test getting status of a specific job."""
         # Create and queue a scan
         scan = Scan(
             timestamp=datetime.utcnow(),
             status='running',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             title='Test Scan',
             triggered_by='test'
         )
         db.add(scan)
         db.commit()
 
-        job_id = app.scheduler.queue_scan(scan.id, sample_config_file)
+        job_id = app.scheduler.queue_scan(scan.id, sample_db_config)
 
         # Get job status
         status = app.scheduler.get_job_status(job_id)
@@ -133,13 +133,13 @@ class TestBackgroundJobs:
         status = app.scheduler.get_job_status('nonexistent_job_id')
         assert status is None
 
-    def test_scan_timing_fields(self, db, sample_config_file):
+    def test_scan_timing_fields(self, db, sample_db_config):
         """Test that scan timing fields are properly set."""
         # Create scan with started_at
         scan = Scan(
             timestamp=datetime.utcnow(),
             status='running',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             title='Test Scan',
             triggered_by='test',
             started_at=datetime.utcnow()
@@ -161,13 +161,13 @@ class TestBackgroundJobs:
         assert scan.completed_at is not None
         assert (scan.completed_at - scan.started_at).total_seconds() >= 0
 
-    def test_scan_error_handling(self, db, sample_config_file):
+    def test_scan_error_handling(self, db, sample_db_config):
         """Test that error messages are stored correctly."""
         # Create failed scan
         scan = Scan(
             timestamp=datetime.utcnow(),
             status='failed',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             title='Failed Scan',
             triggered_by='test',
             started_at=datetime.utcnow(),
@@ -188,7 +188,7 @@ class TestBackgroundJobs:
         assert status['error_message'] == 'Test error message'
 
     @pytest.mark.skip(reason="Requires actual scanner execution - slow test")
-    def test_background_scan_execution(self, app, db, sample_config_file):
+    def test_background_scan_execution(self, app, db, sample_db_config):
         """
         Integration test for actual background scan execution.
 
@@ -200,7 +200,7 @@ class TestBackgroundJobs:
         # Trigger scan
         scan_service = ScanService(db)
         scan_id = scan_service.trigger_scan(
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             triggered_by='test',
             scheduler=app.scheduler
         )

app/tests/test_config_api.py

@@ -0,0 +1,483 @@
+"""
+Integration tests for Config API endpoints.
+
+Tests all config API endpoints including CSV/YAML upload, listing, downloading,
+and deletion with schedule protection.
+"""
+
+import pytest
+import os
+import tempfile
+import shutil
+from web.app import create_app
+from web.models import Base
+from sqlalchemy import create_engine
+from sqlalchemy.orm import scoped_session, sessionmaker
+
+
+@pytest.fixture
+def app():
+    """Create test application"""
+    # Create temporary database
+    test_db = tempfile.mktemp(suffix='.db')
+
+    # Create temporary configs directory
+    temp_configs_dir = tempfile.mkdtemp()
+
+    app = create_app({
+        'TESTING': True,
+        'SQLALCHEMY_DATABASE_URI': f'sqlite:///{test_db}',
+        'SECRET_KEY': 'test-secret-key',
+        'WTF_CSRF_ENABLED': False,
+    })
+
+    # Override configs directory in ConfigService
+    os.environ['CONFIGS_DIR'] = temp_configs_dir
+
+    # Create tables
+    with app.app_context():
+        Base.metadata.create_all(bind=app.db_session.get_bind())
+
+    yield app
+
+    # Cleanup
+    os.unlink(test_db)
+    shutil.rmtree(temp_configs_dir)
+
+
+@pytest.fixture
+def client(app):
+    """Create test client"""
+    return app.test_client()
+
+
+@pytest.fixture
+def auth_headers(client):
+    """Get authentication headers"""
+    # First register and login a user
+    from web.auth.models import User
+
+    with client.application.app_context():
+        # Create test user
+        user = User(username='testuser')
+        user.set_password('testpass')
+        client.application.db_session.add(user)
+        client.application.db_session.commit()
+
+    # Login
+    response = client.post('/auth/login', data={
+        'username': 'testuser',
+        'password': 'testpass'
+    }, follow_redirects=True)
+
+    assert response.status_code == 200
+
+    # Return empty headers (session-based auth)
+    return {}
+
+
+@pytest.fixture
+def sample_csv():
+    """Sample CSV content"""
+    return """scan_title,site_name,ip_address,ping_expected,tcp_ports,udp_ports,services
+Test Scan,Web Servers,10.10.20.4,true,"22,80,443",53,"ssh,http,https"
+Test Scan,Web Servers,10.10.20.5,true,22,,"ssh"
+"""
+
+
+@pytest.fixture
+def sample_yaml():
+    """Sample YAML content"""
+    return """title: Test Scan
+sites:
+  - name: Web Servers
+    ips:
+      - address: 10.10.20.4
+        expected:
+          ping: true
+          tcp_ports: [22, 80, 443]
+          udp_ports: [53]
+          services: [ssh, http, https]
+"""
+
+
+class TestListConfigs:
+    """Tests for GET /api/configs"""
+
+    def test_list_configs_empty(self, client, auth_headers):
+        """Test listing configs when none exist"""
+        response = client.get('/api/configs', headers=auth_headers)
+        assert response.status_code == 200
+
+        data = response.get_json()
+        assert 'configs' in data
+        assert data['configs'] == []
+
+    def test_list_configs_with_files(self, client, auth_headers, app, sample_yaml):
+        """Test listing configs with existing files"""
+        # Create a config file
+        temp_configs_dir = os.environ.get('CONFIGS_DIR', '/app/configs')
+        config_path = os.path.join(temp_configs_dir, 'test-scan.yaml')
+        with open(config_path, 'w') as f:
+            f.write(sample_yaml)
+
+        response = client.get('/api/configs', headers=auth_headers)
+        assert response.status_code == 200
+
+        data = response.get_json()
+        assert len(data['configs']) == 1
+        assert data['configs'][0]['filename'] == 'test-scan.yaml'
+        assert data['configs'][0]['title'] == 'Test Scan'
+        assert 'created_at' in data['configs'][0]
+        assert 'size_bytes' in data['configs'][0]
+        assert 'used_by_schedules' in data['configs'][0]
+
+    def test_list_configs_requires_auth(self, client):
+        """Test that listing configs requires authentication"""
+        response = client.get('/api/configs')
+        assert response.status_code in [401, 302]  # Unauthorized or redirect
+
+
+class TestGetConfig:
+    """Tests for GET /api/configs/<filename>"""
+
+    def test_get_config_valid(self, client, auth_headers, app, sample_yaml):
+        """Test getting a valid config file"""
+        # Create a config file
+        temp_configs_dir = os.environ.get('CONFIGS_DIR', '/app/configs')
+        config_path = os.path.join(temp_configs_dir, 'test-scan.yaml')
+        with open(config_path, 'w') as f:
+            f.write(sample_yaml)
+
+        response = client.get('/api/configs/test-scan.yaml', headers=auth_headers)
+        assert response.status_code == 200
+
+        data = response.get_json()
+        assert data['filename'] == 'test-scan.yaml'
+        assert 'content' in data
+        assert 'parsed' in data
+        assert data['parsed']['title'] == 'Test Scan'
+
+    def test_get_config_not_found(self, client, auth_headers):
+        """Test getting non-existent config"""
+        response = client.get('/api/configs/nonexistent.yaml', headers=auth_headers)
+        assert response.status_code == 404
+
+        data = response.get_json()
+        assert 'error' in data
+
+    def test_get_config_requires_auth(self, client):
+        """Test that getting config requires authentication"""
+        response = client.get('/api/configs/test.yaml')
+        assert response.status_code in [401, 302]
+
+
+class TestUploadCSV:
+    """Tests for POST /api/configs/upload-csv"""
+
+    def test_upload_csv_valid(self, client, auth_headers, sample_csv):
+        """Test uploading valid CSV"""
+        from io import BytesIO
+
+        data = {
+            'file': (BytesIO(sample_csv.encode('utf-8')), 'test.csv')
+        }
+
+        response = client.post('/api/configs/upload-csv', data=data,
+                              headers=auth_headers, content_type='multipart/form-data')
+        assert response.status_code == 200
+
+        result = response.get_json()
+        assert result['success'] is True
+        assert 'filename' in result
+        assert result['filename'].endswith('.yaml')
+        assert 'preview' in result
+
+    def test_upload_csv_no_file(self, client, auth_headers):
+        """Test uploading without file"""
+        response = client.post('/api/configs/upload-csv', data={},
+                              headers=auth_headers, content_type='multipart/form-data')
+        assert response.status_code == 400
+
+        data = response.get_json()
+        assert 'error' in data
+
+    def test_upload_csv_invalid_format(self, client, auth_headers):
+        """Test uploading invalid CSV"""
+        from io import BytesIO
+
+        invalid_csv = "not,a,valid,csv\nmissing,columns"
+
+        data = {
+            'file': (BytesIO(invalid_csv.encode('utf-8')), 'test.csv')
+        }
+
+        response = client.post('/api/configs/upload-csv', data=data,
+                              headers=auth_headers, content_type='multipart/form-data')
+        assert response.status_code == 400
+
+        result = response.get_json()
+        assert 'error' in result
+
+    def test_upload_csv_wrong_extension(self, client, auth_headers):
+        """Test uploading file with wrong extension"""
+        from io import BytesIO
+
+        data = {
+            'file': (BytesIO(b'test'), 'test.txt')
+        }
+
+        response = client.post('/api/configs/upload-csv', data=data,
+                              headers=auth_headers, content_type='multipart/form-data')
+        assert response.status_code == 400
+
+    def test_upload_csv_duplicate_filename(self, client, auth_headers, sample_csv):
+        """Test uploading CSV that generates duplicate filename"""
+        from io import BytesIO
+
+        data = {
+            'file': (BytesIO(sample_csv.encode('utf-8')), 'test.csv')
+        }
+
+        # Upload first time
+        response1 = client.post('/api/configs/upload-csv', data=data,
+                               headers=auth_headers, content_type='multipart/form-data')
+        assert response1.status_code == 200
+
+        # Upload second time (should fail)
+        response2 = client.post('/api/configs/upload-csv', data=data,
+                               headers=auth_headers, content_type='multipart/form-data')
+        assert response2.status_code == 400
+
+    def test_upload_csv_requires_auth(self, client, sample_csv):
+        """Test that uploading CSV requires authentication"""
+        from io import BytesIO
+
+        data = {
+            'file': (BytesIO(sample_csv.encode('utf-8')), 'test.csv')
+        }
+
+        response = client.post('/api/configs/upload-csv', data=data,
+                              content_type='multipart/form-data')
+        assert response.status_code in [401, 302]
+
+
+class TestUploadYAML:
+    """Tests for POST /api/configs/upload-yaml"""
+
+    def test_upload_yaml_valid(self, client, auth_headers, sample_yaml):
+        """Test uploading valid YAML"""
+        from io import BytesIO
+
+        data = {
+            'file': (BytesIO(sample_yaml.encode('utf-8')), 'test.yaml')
+        }
+
+        response = client.post('/api/configs/upload-yaml', data=data,
+                              headers=auth_headers, content_type='multipart/form-data')
+        assert response.status_code == 200
+
+        result = response.get_json()
+        assert result['success'] is True
+        assert 'filename' in result
+
+    def test_upload_yaml_no_file(self, client, auth_headers):
+        """Test uploading without file"""
+        response = client.post('/api/configs/upload-yaml', data={},
+                              headers=auth_headers, content_type='multipart/form-data')
+        assert response.status_code == 400
+
+    def test_upload_yaml_invalid_syntax(self, client, auth_headers):
+        """Test uploading YAML with invalid syntax"""
+        from io import BytesIO
+
+        invalid_yaml = "invalid: yaml: syntax: ["
+
+        data = {
+            'file': (BytesIO(invalid_yaml.encode('utf-8')), 'test.yaml')
+        }
+
+        response = client.post('/api/configs/upload-yaml', data=data,
+                              headers=auth_headers, content_type='multipart/form-data')
+        assert response.status_code == 400
+
+    def test_upload_yaml_missing_required_fields(self, client, auth_headers):
+        """Test uploading YAML missing required fields"""
+        from io import BytesIO
+
+        invalid_yaml = """sites:
+  - name: Test
+    ips:
+      - address: 10.0.0.1
+"""
+
+        data = {
+            'file': (BytesIO(invalid_yaml.encode('utf-8')), 'test.yaml')
+        }
+
+        response = client.post('/api/configs/upload-yaml', data=data,
+                              headers=auth_headers, content_type='multipart/form-data')
+        assert response.status_code == 400
+
+    def test_upload_yaml_wrong_extension(self, client, auth_headers):
+        """Test uploading file with wrong extension"""
+        from io import BytesIO
+
+        data = {
+            'file': (BytesIO(b'test'), 'test.txt')
+        }
+
+        response = client.post('/api/configs/upload-yaml', data=data,
+                              headers=auth_headers, content_type='multipart/form-data')
+        assert response.status_code == 400
+
+    def test_upload_yaml_requires_auth(self, client, sample_yaml):
+        """Test that uploading YAML requires authentication"""
+        from io import BytesIO
+
+        data = {
+            'file': (BytesIO(sample_yaml.encode('utf-8')), 'test.yaml')
+        }
+
+        response = client.post('/api/configs/upload-yaml', data=data,
+                              content_type='multipart/form-data')
+        assert response.status_code in [401, 302]
+
+
+class TestDownloadTemplate:
+    """Tests for GET /api/configs/template"""
+
+    def test_download_template(self, client, auth_headers):
+        """Test downloading CSV template"""
+        response = client.get('/api/configs/template', headers=auth_headers)
+        assert response.status_code == 200
+        assert response.content_type == 'text/csv; charset=utf-8'
+        assert b'scan_title,site_name,ip_address' in response.data
+
+    def test_download_template_requires_auth(self, client):
+        """Test that downloading template requires authentication"""
+        response = client.get('/api/configs/template')
+        assert response.status_code in [401, 302]
+
+
+class TestDownloadConfig:
+    """Tests for GET /api/configs/<filename>/download"""
+
+    def test_download_config_valid(self, client, auth_headers, app, sample_yaml):
+        """Test downloading existing config"""
+        # Create a config file
+        temp_configs_dir = os.environ.get('CONFIGS_DIR', '/app/configs')
+        config_path = os.path.join(temp_configs_dir, 'test-scan.yaml')
+        with open(config_path, 'w') as f:
+            f.write(sample_yaml)
+
+        response = client.get('/api/configs/test-scan.yaml/download', headers=auth_headers)
+        assert response.status_code == 200
+        assert response.content_type == 'application/x-yaml; charset=utf-8'
+        assert b'title: Test Scan' in response.data
+
+    def test_download_config_not_found(self, client, auth_headers):
+        """Test downloading non-existent config"""
+        response = client.get('/api/configs/nonexistent.yaml/download', headers=auth_headers)
+        assert response.status_code == 404
+
+    def test_download_config_requires_auth(self, client):
+        """Test that downloading config requires authentication"""
+        response = client.get('/api/configs/test.yaml/download')
+        assert response.status_code in [401, 302]
+
+
+class TestDeleteConfig:
+    """Tests for DELETE /api/configs/<filename>"""
+
+    def test_delete_config_valid(self, client, auth_headers, app, sample_yaml):
+        """Test deleting a config file"""
+        # Create a config file
+        temp_configs_dir = os.environ.get('CONFIGS_DIR', '/app/configs')
+        config_path = os.path.join(temp_configs_dir, 'test-scan.yaml')
+        with open(config_path, 'w') as f:
+            f.write(sample_yaml)
+
+        response = client.delete('/api/configs/test-scan.yaml', headers=auth_headers)
+        assert response.status_code == 200
+
+        data = response.get_json()
+        assert data['success'] is True
+
+        # Verify file is deleted
+        assert not os.path.exists(config_path)
+
+    def test_delete_config_not_found(self, client, auth_headers):
+        """Test deleting non-existent config"""
+        response = client.delete('/api/configs/nonexistent.yaml', headers=auth_headers)
+        assert response.status_code == 404
+
+    def test_delete_config_requires_auth(self, client):
+        """Test that deleting config requires authentication"""
+        response = client.delete('/api/configs/test.yaml')
+        assert response.status_code in [401, 302]
+
+
+class TestEndToEndWorkflow:
+    """End-to-end workflow tests"""
+
+    def test_complete_csv_workflow(self, client, auth_headers, sample_csv):
+        """Test complete CSV upload workflow"""
+        from io import BytesIO
+
+        # 1. Download template
+        response = client.get('/api/configs/template', headers=auth_headers)
+        assert response.status_code == 200
+
+        # 2. Upload CSV
+        data = {
+            'file': (BytesIO(sample_csv.encode('utf-8')), 'workflow-test.csv')
+        }
+        response = client.post('/api/configs/upload-csv', data=data,
+                              headers=auth_headers, content_type='multipart/form-data')
+        assert response.status_code == 200
+        result = response.get_json()
+        filename = result['filename']
+
+        # 3. List configs (should include new one)
+        response = client.get('/api/configs', headers=auth_headers)
+        assert response.status_code == 200
+        configs = response.get_json()['configs']
+        assert any(c['filename'] == filename for c in configs)
+
+        # 4. Get config details
+        response = client.get(f'/api/configs/{filename}', headers=auth_headers)
+        assert response.status_code == 200
+
+        # 5. Download config
+        response = client.get(f'/api/configs/{filename}/download', headers=auth_headers)
+        assert response.status_code == 200
+
+        # 6. Delete config
+        response = client.delete(f'/api/configs/{filename}', headers=auth_headers)
+        assert response.status_code == 200
+
+        # 7. Verify deletion
+        response = client.get(f'/api/configs/{filename}', headers=auth_headers)
+        assert response.status_code == 404
+
+    def test_yaml_upload_workflow(self, client, auth_headers, sample_yaml):
+        """Test YAML upload workflow"""
+        from io import BytesIO
+
+        # Upload YAML
+        data = {
+            'file': (BytesIO(sample_yaml.encode('utf-8')), 'yaml-workflow.yaml')
+        }
+        response = client.post('/api/configs/upload-yaml', data=data,
+                              headers=auth_headers, content_type='multipart/form-data')
+        assert response.status_code == 200
+
+        filename = response.get_json()['filename']
+
+        # Verify it exists
+        response = client.get(f'/api/configs/{filename}', headers=auth_headers)
+        assert response.status_code == 200
+
+        # Clean up
+        client.delete(f'/api/configs/{filename}', headers=auth_headers)

app/tests/test_config_service.py

@@ -0,0 +1,545 @@
+"""
+Unit tests for Config Service
+
+Tests the ConfigService class which manages scan configuration files.
+"""
+
+import pytest
+import os
+import yaml
+import tempfile
+import shutil
+from web.services.config_service import ConfigService
+
+
+class TestConfigService:
+    """Test suite for ConfigService"""
+
+    @pytest.fixture
+    def temp_configs_dir(self):
+        """Create a temporary directory for config files"""
+        temp_dir = tempfile.mkdtemp()
+        yield temp_dir
+        shutil.rmtree(temp_dir)
+
+    @pytest.fixture
+    def service(self, temp_configs_dir):
+        """Create a ConfigService instance with temp directory"""
+        return ConfigService(configs_dir=temp_configs_dir)
+
+    @pytest.fixture
+    def sample_yaml_config(self):
+        """Sample YAML config content"""
+        return """title: Test Scan
+sites:
+  - name: Web Servers
+    ips:
+      - address: 10.10.20.4
+        expected:
+          ping: true
+          tcp_ports: [22, 80, 443]
+          udp_ports: [53]
+          services: [ssh, http, https]
+"""
+
+    @pytest.fixture
+    def sample_csv_content(self):
+        """Sample CSV content"""
+        return """scan_title,site_name,ip_address,ping_expected,tcp_ports,udp_ports,services
+Test Scan,Web Servers,10.10.20.4,true,"22,80,443",53,"ssh,http,https"
+Test Scan,Web Servers,10.10.20.5,true,22,,"ssh"
+"""
+
+    def test_list_configs_empty_directory(self, service):
+        """Test listing configs when directory is empty"""
+        configs = service.list_configs()
+        assert configs == []
+
+    def test_list_configs_with_files(self, service, temp_configs_dir, sample_yaml_config):
+        """Test listing configs with existing files"""
+        # Create a config file
+        config_path = os.path.join(temp_configs_dir, 'test-scan.yaml')
+        with open(config_path, 'w') as f:
+            f.write(sample_yaml_config)
+
+        configs = service.list_configs()
+        assert len(configs) == 1
+        assert configs[0]['filename'] == 'test-scan.yaml'
+        assert configs[0]['title'] == 'Test Scan'
+        assert 'created_at' in configs[0]
+        assert 'size_bytes' in configs[0]
+        assert 'used_by_schedules' in configs[0]
+
+    def test_list_configs_ignores_non_yaml_files(self, service, temp_configs_dir):
+        """Test that non-YAML files are ignored"""
+        # Create non-YAML files
+        with open(os.path.join(temp_configs_dir, 'test.txt'), 'w') as f:
+            f.write('not a yaml file')
+        with open(os.path.join(temp_configs_dir, 'readme.md'), 'w') as f:
+            f.write('# README')
+
+        configs = service.list_configs()
+        assert len(configs) == 0
+
+    def test_get_config_valid(self, service, temp_configs_dir, sample_yaml_config):
+        """Test getting a valid config file"""
+        # Create a config file
+        config_path = os.path.join(temp_configs_dir, 'test-scan.yaml')
+        with open(config_path, 'w') as f:
+            f.write(sample_yaml_config)
+
+        result = service.get_config('test-scan.yaml')
+        assert result['filename'] == 'test-scan.yaml'
+        assert 'content' in result
+        assert 'parsed' in result
+        assert result['parsed']['title'] == 'Test Scan'
+        assert len(result['parsed']['sites']) == 1
+
+    def test_get_config_not_found(self, service):
+        """Test getting a non-existent config"""
+        with pytest.raises(FileNotFoundError, match="not found"):
+            service.get_config('nonexistent.yaml')
+
+    def test_get_config_invalid_yaml(self, service, temp_configs_dir):
+        """Test getting a config with invalid YAML syntax"""
+        # Create invalid YAML file
+        config_path = os.path.join(temp_configs_dir, 'invalid.yaml')
+        with open(config_path, 'w') as f:
+            f.write("invalid: yaml: syntax: [")
+
+        with pytest.raises(ValueError, match="Invalid YAML syntax"):
+            service.get_config('invalid.yaml')
+
+    def test_create_from_yaml_valid(self, service, sample_yaml_config):
+        """Test creating config from valid YAML"""
+        filename = service.create_from_yaml('test-scan.yaml', sample_yaml_config)
+        assert filename == 'test-scan.yaml'
+        assert service.config_exists('test-scan.yaml')
+
+        # Verify content
+        result = service.get_config('test-scan.yaml')
+        assert result['parsed']['title'] == 'Test Scan'
+
+    def test_create_from_yaml_adds_extension(self, service, sample_yaml_config):
+        """Test that .yaml extension is added if missing"""
+        filename = service.create_from_yaml('test-scan', sample_yaml_config)
+        assert filename == 'test-scan.yaml'
+        assert service.config_exists('test-scan.yaml')
+
+    def test_create_from_yaml_sanitizes_filename(self, service, sample_yaml_config):
+        """Test that filename is sanitized"""
+        filename = service.create_from_yaml('../../../etc/test.yaml', sample_yaml_config)
+        # secure_filename should remove path traversal
+        assert '..' not in filename
+        assert '/' not in filename
+
+    def test_create_from_yaml_duplicate_filename(self, service, temp_configs_dir, sample_yaml_config):
+        """Test creating config with duplicate filename"""
+        # Create first config
+        service.create_from_yaml('test-scan.yaml', sample_yaml_config)
+
+        # Try to create duplicate
+        with pytest.raises(ValueError, match="already exists"):
+            service.create_from_yaml('test-scan.yaml', sample_yaml_config)
+
+    def test_create_from_yaml_invalid_syntax(self, service):
+        """Test creating config with invalid YAML syntax"""
+        invalid_yaml = "invalid: yaml: syntax: ["
+
+        with pytest.raises(ValueError, match="Invalid YAML syntax"):
+            service.create_from_yaml('test.yaml', invalid_yaml)
+
+    def test_create_from_yaml_invalid_structure(self, service):
+        """Test creating config with invalid structure (missing title)"""
+        invalid_config = """sites:
+  - name: Test
+    ips:
+      - address: 10.0.0.1
+        expected:
+          ping: true
+"""
+
+        with pytest.raises(ValueError, match="Missing required field: 'title'"):
+            service.create_from_yaml('test.yaml', invalid_config)
+
+    def test_create_from_csv_valid(self, service, sample_csv_content):
+        """Test creating config from valid CSV"""
+        filename, yaml_content = service.create_from_csv(sample_csv_content)
+        assert filename == 'test-scan.yaml'
+        assert service.config_exists(filename)
+
+        # Verify YAML was created correctly
+        result = service.get_config(filename)
+        assert result['parsed']['title'] == 'Test Scan'
+        assert len(result['parsed']['sites']) == 1
+        assert len(result['parsed']['sites'][0]['ips']) == 2
+
+    def test_create_from_csv_with_suggested_filename(self, service, sample_csv_content):
+        """Test creating config with suggested filename"""
+        filename, yaml_content = service.create_from_csv(sample_csv_content, 'custom-name.yaml')
+        assert filename == 'custom-name.yaml'
+        assert service.config_exists(filename)
+
+    def test_create_from_csv_invalid(self, service):
+        """Test creating config from invalid CSV"""
+        invalid_csv = """scan_title,site_name,ip_address
+Missing,Columns,Here
+"""
+
+        with pytest.raises(ValueError, match="CSV parsing failed"):
+            service.create_from_csv(invalid_csv)
+
+    def test_create_from_csv_duplicate_filename(self, service, sample_csv_content):
+        """Test creating CSV config with duplicate filename"""
+        # Create first config
+        service.create_from_csv(sample_csv_content)
+
+        # Try to create duplicate (same title generates same filename)
+        with pytest.raises(ValueError, match="already exists"):
+            service.create_from_csv(sample_csv_content)
+
+    def test_delete_config_valid(self, service, temp_configs_dir, sample_yaml_config):
+        """Test deleting a config file"""
+        # Create a config file
+        config_path = os.path.join(temp_configs_dir, 'test-scan.yaml')
+        with open(config_path, 'w') as f:
+            f.write(sample_yaml_config)
+
+        assert service.config_exists('test-scan.yaml')
+        service.delete_config('test-scan.yaml')
+        assert not service.config_exists('test-scan.yaml')
+
+    def test_delete_config_not_found(self, service):
+        """Test deleting non-existent config"""
+        with pytest.raises(FileNotFoundError, match="not found"):
+            service.delete_config('nonexistent.yaml')
+
+    def test_delete_config_used_by_schedule(self, service, temp_configs_dir, sample_yaml_config, monkeypatch):
+        """Test deleting config that is used by schedules - should cascade delete schedules"""
+        # Create a config file
+        config_path = os.path.join(temp_configs_dir, 'test-scan.yaml')
+        with open(config_path, 'w') as f:
+            f.write(sample_yaml_config)
+
+        # Mock schedule service interactions
+        deleted_schedule_ids = []
+
+        class MockScheduleService:
+            def __init__(self, db):
+                self.db = db
+
+            def list_schedules(self, page=1, per_page=10000):
+                return {
+                    'schedules': [
+                        {
+                            'id': 1,
+                            'name': 'Daily Scan',
+                            'config_file': 'test-scan.yaml',
+                            'enabled': True
+                        },
+                        {
+                            'id': 2,
+                            'name': 'Weekly Audit',
+                            'config_file': 'test-scan.yaml',
+                            'enabled': False  # Disabled schedule should also be deleted
+                        }
+                    ]
+                }
+
+            def delete_schedule(self, schedule_id):
+                deleted_schedule_ids.append(schedule_id)
+                return True
+
+        # Mock the ScheduleService import
+        import sys
+        from unittest.mock import MagicMock
+        mock_module = MagicMock()
+        mock_module.ScheduleService = MockScheduleService
+        monkeypatch.setitem(sys.modules, 'web.services.schedule_service', mock_module)
+
+        # Mock current_app
+        mock_app = MagicMock()
+        mock_app.db_session = MagicMock()
+
+        import flask
+        monkeypatch.setattr(flask, 'current_app', mock_app)
+
+        # Delete the config - should cascade delete associated schedules
+        service.delete_config('test-scan.yaml')
+
+        # Config should be deleted
+        assert not service.config_exists('test-scan.yaml')
+
+        # Both schedules (enabled and disabled) should be deleted
+        assert deleted_schedule_ids == [1, 2]
+
+    def test_validate_config_content_valid(self, service):
+        """Test validating valid config content"""
+        valid_config = {
+            'title': 'Test Scan',
+            'sites': [
+                {
+                    'name': 'Web Servers',
+                    'ips': [
+                        {
+                            'address': '10.10.20.4',
+                            'expected': {
+                                'ping': True,
+                                'tcp_ports': [22, 80, 443],
+                                'udp_ports': [53]
+                            }
+                        }
+                    ]
+                }
+            ]
+        }
+
+        is_valid, error = service.validate_config_content(valid_config)
+        assert is_valid is True
+        assert error == ""
+
+    def test_validate_config_content_not_dict(self, service):
+        """Test validating non-dict content"""
+        is_valid, error = service.validate_config_content(['not', 'a', 'dict'])
+        assert is_valid is False
+        assert 'must be a dictionary' in error
+
+    def test_validate_config_content_missing_title(self, service):
+        """Test validating config without title"""
+        config = {
+            'sites': []
+        }
+
+        is_valid, error = service.validate_config_content(config)
+        assert is_valid is False
+        assert "Missing required field: 'title'" in error
+
+    def test_validate_config_content_missing_sites(self, service):
+        """Test validating config without sites"""
+        config = {
+            'title': 'Test'
+        }
+
+        is_valid, error = service.validate_config_content(config)
+        assert is_valid is False
+        assert "Missing required field: 'sites'" in error
+
+    def test_validate_config_content_empty_title(self, service):
+        """Test validating config with empty title"""
+        config = {
+            'title': '',
+            'sites': []
+        }
+
+        is_valid, error = service.validate_config_content(config)
+        assert is_valid is False
+        assert "non-empty string" in error
+
+    def test_validate_config_content_sites_not_list(self, service):
+        """Test validating config with sites as non-list"""
+        config = {
+            'title': 'Test',
+            'sites': 'not a list'
+        }
+
+        is_valid, error = service.validate_config_content(config)
+        assert is_valid is False
+        assert "must be a list" in error
+
+    def test_validate_config_content_no_sites(self, service):
+        """Test validating config with empty sites list"""
+        config = {
+            'title': 'Test',
+            'sites': []
+        }
+
+        is_valid, error = service.validate_config_content(config)
+        assert is_valid is False
+        assert "at least one site" in error
+
+    def test_validate_config_content_site_missing_name(self, service):
+        """Test validating site without name"""
+        config = {
+            'title': 'Test',
+            'sites': [
+                {
+                    'ips': []
+                }
+            ]
+        }
+
+        is_valid, error = service.validate_config_content(config)
+        assert is_valid is False
+        assert "missing required field: 'name'" in error
+
+    def test_validate_config_content_site_missing_ips(self, service):
+        """Test validating site without ips"""
+        config = {
+            'title': 'Test',
+            'sites': [
+                {
+                    'name': 'Test Site'
+                }
+            ]
+        }
+
+        is_valid, error = service.validate_config_content(config)
+        assert is_valid is False
+        assert "missing required field: 'ips'" in error
+
+    def test_validate_config_content_site_no_ips(self, service):
+        """Test validating site with empty ips list"""
+        config = {
+            'title': 'Test',
+            'sites': [
+                {
+                    'name': 'Test Site',
+                    'ips': []
+                }
+            ]
+        }
+
+        is_valid, error = service.validate_config_content(config)
+        assert is_valid is False
+        assert "at least one IP" in error
+
+    def test_validate_config_content_ip_missing_address(self, service):
+        """Test validating IP without address"""
+        config = {
+            'title': 'Test',
+            'sites': [
+                {
+                    'name': 'Test Site',
+                    'ips': [
+                        {
+                            'expected': {}
+                        }
+                    ]
+                }
+            ]
+        }
+
+        is_valid, error = service.validate_config_content(config)
+        assert is_valid is False
+        assert "missing required field: 'address'" in error
+
+    def test_validate_config_content_ip_missing_expected(self, service):
+        """Test validating IP without expected"""
+        config = {
+            'title': 'Test',
+            'sites': [
+                {
+                    'name': 'Test Site',
+                    'ips': [
+                        {
+                            'address': '10.0.0.1'
+                        }
+                    ]
+                }
+            ]
+        }
+
+        is_valid, error = service.validate_config_content(config)
+        assert is_valid is False
+        assert "missing required field: 'expected'" in error
+
+    def test_generate_filename_from_title_simple(self, service):
+        """Test generating filename from simple title"""
+        filename = service.generate_filename_from_title('Production Scan')
+        assert filename == 'production-scan.yaml'
+
+    def test_generate_filename_from_title_special_chars(self, service):
+        """Test generating filename with special characters"""
+        filename = service.generate_filename_from_title('Prod Scan (2025)!')
+        assert filename == 'prod-scan-2025.yaml'
+        assert '(' not in filename
+        assert ')' not in filename
+        assert '!' not in filename
+
+    def test_generate_filename_from_title_multiple_spaces(self, service):
+        """Test generating filename with multiple spaces"""
+        filename = service.generate_filename_from_title('Test   Multiple    Spaces')
+        assert filename == 'test-multiple-spaces.yaml'
+        # Should not have consecutive hyphens
+        assert '--' not in filename
+
+    def test_generate_filename_from_title_leading_trailing_spaces(self, service):
+        """Test generating filename with leading/trailing spaces"""
+        filename = service.generate_filename_from_title('  Test Scan  ')
+        assert filename == 'test-scan.yaml'
+        assert not filename.startswith('-')
+        assert not filename.endswith('-.yaml')
+
+    def test_generate_filename_from_title_long(self, service):
+        """Test generating filename from long title"""
+        long_title = 'A' * 300
+        filename = service.generate_filename_from_title(long_title)
+        # Should be limited to 200 chars (195 + .yaml)
+        assert len(filename) <= 200
+
+    def test_generate_filename_from_title_empty(self, service):
+        """Test generating filename from empty title"""
+        filename = service.generate_filename_from_title('')
+        assert filename == 'config.yaml'
+
+    def test_generate_filename_from_title_only_special_chars(self, service):
+        """Test generating filename from title with only special characters"""
+        filename = service.generate_filename_from_title('!@#$%^&*()')
+        assert filename == 'config.yaml'
+
+    def test_get_config_path(self, service, temp_configs_dir):
+        """Test getting config path"""
+        path = service.get_config_path('test.yaml')
+        assert path == os.path.join(temp_configs_dir, 'test.yaml')
+
+    def test_config_exists_true(self, service, temp_configs_dir, sample_yaml_config):
+        """Test config_exists returns True for existing file"""
+        config_path = os.path.join(temp_configs_dir, 'test-scan.yaml')
+        with open(config_path, 'w') as f:
+            f.write(sample_yaml_config)
+
+        assert service.config_exists('test-scan.yaml') is True
+
+    def test_config_exists_false(self, service):
+        """Test config_exists returns False for non-existent file"""
+        assert service.config_exists('nonexistent.yaml') is False
+
+    def test_get_schedules_using_config_none(self, service):
+        """Test getting schedules when none use the config"""
+        schedules = service.get_schedules_using_config('test.yaml')
+        # Should return empty list (ScheduleService might not exist in test env)
+        assert isinstance(schedules, list)
+
+    def test_list_configs_sorted_by_date(self, service, temp_configs_dir, sample_yaml_config):
+        """Test that configs are sorted by creation date (most recent first)"""
+        import time
+
+        # Create first config
+        config1_path = os.path.join(temp_configs_dir, 'config1.yaml')
+        with open(config1_path, 'w') as f:
+            f.write(sample_yaml_config)
+
+        time.sleep(0.1)  # Ensure different timestamps
+
+        # Create second config
+        config2_path = os.path.join(temp_configs_dir, 'config2.yaml')
+        with open(config2_path, 'w') as f:
+            f.write(sample_yaml_config)
+
+        configs = service.list_configs()
+        assert len(configs) == 2
+        # Most recent should be first
+        assert configs[0]['filename'] == 'config2.yaml'
+        assert configs[1]['filename'] == 'config1.yaml'
+
+    def test_list_configs_handles_parse_errors(self, service, temp_configs_dir):
+        """Test that list_configs handles files that can't be parsed"""
+        # Create invalid YAML file
+        config_path = os.path.join(temp_configs_dir, 'invalid.yaml')
+        with open(config_path, 'w') as f:
+            f.write("invalid: yaml: [")
+
+        # Should not raise error, just use filename as title
+        configs = service.list_configs()
+        assert len(configs) == 1
+        assert configs[0]['filename'] == 'invalid.yaml'

app/tests/test_scan_api.py

@@ -37,14 +37,14 @@ class TestScanAPIEndpoints:
         assert len(data['scans']) == 1
         assert data['scans'][0]['id'] == sample_scan.id
 
-    def test_list_scans_pagination(self, client, db):
+    def test_list_scans_pagination(self, client, db, sample_db_config):
         """Test scan list pagination."""
         # Create 25 scans
         for i in range(25):
             scan = Scan(
                 timestamp=datetime.utcnow(),
                 status='completed',
-                config_file=f'/app/configs/test{i}.yaml',
+                config_id=sample_db_config.id,
                 title=f'Test Scan {i}',
                 triggered_by='test'
             )
@@ -81,7 +81,7 @@ class TestScanAPIEndpoints:
             scan = Scan(
                 timestamp=datetime.utcnow(),
                 status=status,
-                config_file='/app/configs/test.yaml',
+                config_id=1,
                 title=f'{status.capitalize()} Scan',
                 triggered_by='test'
             )
@@ -123,10 +123,10 @@ class TestScanAPIEndpoints:
         assert 'error' in data
         assert data['error'] == 'Not found'
 
-    def test_trigger_scan_success(self, client, db, sample_config_file):
+    def test_trigger_scan_success(self, client, db, sample_db_config):
         """Test triggering a new scan."""
         response = client.post('/api/scans',
-            json={'config_file': str(sample_config_file)},
+            json={'config_id': sample_db_config.id},
             content_type='application/json'
         )
         assert response.status_code == 201
@@ -142,8 +142,8 @@ class TestScanAPIEndpoints:
         assert scan.status == 'running'
         assert scan.triggered_by == 'api'
 
-    def test_trigger_scan_missing_config_file(self, client, db):
-        """Test triggering scan without config_file."""
+    def test_trigger_scan_missing_config_id(self, client, db):
+        """Test triggering scan without config_id."""
         response = client.post('/api/scans',
             json={},
             content_type='application/json'
@@ -152,12 +152,12 @@ class TestScanAPIEndpoints:
 
         data = json.loads(response.data)
         assert 'error' in data
-        assert 'config_file is required' in data['message']
+        assert 'config_id is required' in data['message']
 
-    def test_trigger_scan_invalid_config_file(self, client, db):
-        """Test triggering scan with non-existent config file."""
+    def test_trigger_scan_invalid_config_id(self, client, db):
+        """Test triggering scan with non-existent config."""
         response = client.post('/api/scans',
-            json={'config_file': '/nonexistent/config.yaml'},
+            json={'config_id': 99999},
             content_type='application/json'
         )
         assert response.status_code == 400
@@ -222,7 +222,7 @@ class TestScanAPIEndpoints:
         assert 'error' in data
         assert 'message' in data
 
-    def test_scan_workflow_integration(self, client, db, sample_config_file):
+    def test_scan_workflow_integration(self, client, db, sample_db_config):
         """
         Test complete scan workflow: trigger → status → retrieve → delete.
 
@@ -231,7 +231,7 @@ class TestScanAPIEndpoints:
         """
         # Step 1: Trigger scan
         response = client.post('/api/scans',
-            json={'config_file': str(sample_config_file)},
+            json={'config_id': sample_db_config.id},
             content_type='application/json'
         )
         assert response.status_code == 201

app/tests/test_scan_comparison.py

@@ -17,10 +17,10 @@ class TestScanComparison:
     """Tests for scan comparison methods."""
 
     @pytest.fixture
-    def scan1_data(self, test_db, sample_config_file):
+    def scan1_data(self, test_db, sample_db_config):
         """Create first scan with test data."""
         service = ScanService(test_db)
-        scan_id = service.trigger_scan(sample_config_file, triggered_by='manual')
+        scan_id = service.trigger_scan(sample_db_config, triggered_by='manual')
 
         # Get scan and add some test data
         scan = test_db.query(Scan).filter(Scan.id == scan_id).first()
@@ -77,10 +77,10 @@ class TestScanComparison:
         return scan_id
 
     @pytest.fixture
-    def scan2_data(self, test_db, sample_config_file):
+    def scan2_data(self, test_db, sample_db_config):
         """Create second scan with modified test data."""
         service = ScanService(test_db)
-        scan_id = service.trigger_scan(sample_config_file, triggered_by='manual')
+        scan_id = service.trigger_scan(sample_db_config, triggered_by='manual')
 
         # Get scan and add some test data
         scan = test_db.query(Scan).filter(Scan.id == scan_id).first()

app/tests/test_scan_service.py

@@ -13,49 +13,42 @@ from web.services.scan_service import ScanService
 class TestScanServiceTrigger:
     """Tests for triggering scans."""
 
-    def test_trigger_scan_valid_config(self, test_db, sample_config_file):
-        """Test triggering a scan with valid config file."""
-        service = ScanService(test_db)
+    def test_trigger_scan_valid_config(self, db, sample_db_config):
+        """Test triggering a scan with valid config."""
+        service = ScanService(db)
 
-        scan_id = service.trigger_scan(sample_config_file, triggered_by='manual')
+        scan_id = service.trigger_scan(config_id=sample_db_config.id, triggered_by='manual')
 
         # Verify scan created
         assert scan_id is not None
         assert isinstance(scan_id, int)
 
         # Verify scan in database
-        scan = test_db.query(Scan).filter(Scan.id == scan_id).first()
+        scan = db.query(Scan).filter(Scan.id == scan_id).first()
         assert scan is not None
         assert scan.status == 'running'
         assert scan.title == 'Test Scan'
         assert scan.triggered_by == 'manual'
-        assert scan.config_file == sample_config_file
+        assert scan.config_id == sample_db_config.id
 
-    def test_trigger_scan_invalid_config(self, test_db, sample_invalid_config_file):
-        """Test triggering a scan with invalid config file."""
-        service = ScanService(test_db)
+    def test_trigger_scan_invalid_config(self, db):
+        """Test triggering a scan with invalid config ID."""
+        service = ScanService(db)
 
-        with pytest.raises(ValueError, match="Invalid config file"):
-            service.trigger_scan(sample_invalid_config_file)
+        with pytest.raises(ValueError, match="not found"):
+            service.trigger_scan(config_id=99999)
 
-    def test_trigger_scan_nonexistent_file(self, test_db):
-        """Test triggering a scan with nonexistent config file."""
-        service = ScanService(test_db)
-
-        with pytest.raises(ValueError, match="does not exist"):
-            service.trigger_scan('/nonexistent/config.yaml')
-
-    def test_trigger_scan_with_schedule(self, test_db, sample_config_file):
+    def test_trigger_scan_with_schedule(self, db, sample_db_config):
         """Test triggering a scan via schedule."""
-        service = ScanService(test_db)
+        service = ScanService(db)
 
         scan_id = service.trigger_scan(
-            sample_config_file,
+            config_id=sample_db_config.id,
             triggered_by='scheduled',
             schedule_id=42
         )
 
-        scan = test_db.query(Scan).filter(Scan.id == scan_id).first()
+        scan = db.query(Scan).filter(Scan.id == scan_id).first()
         assert scan.triggered_by == 'scheduled'
         assert scan.schedule_id == 42
 
@@ -63,19 +56,19 @@ class TestScanServiceTrigger:
 class TestScanServiceGet:
     """Tests for retrieving scans."""
 
-    def test_get_scan_not_found(self, test_db):
+    def test_get_scan_not_found(self, db):
         """Test getting a nonexistent scan."""
-        service = ScanService(test_db)
+        service = ScanService(db)
 
         result = service.get_scan(999)
         assert result is None
 
-    def test_get_scan_found(self, test_db, sample_config_file):
+    def test_get_scan_found(self, db, sample_db_config):
         """Test getting an existing scan."""
-        service = ScanService(test_db)
+        service = ScanService(db)
 
         # Create a scan
-        scan_id = service.trigger_scan(sample_config_file)
+        scan_id = service.trigger_scan(config_id=sample_db_config.id)
 
         # Retrieve it
         result = service.get_scan(scan_id)
@@ -90,9 +83,9 @@ class TestScanServiceGet:
 class TestScanServiceList:
     """Tests for listing scans."""
 
-    def test_list_scans_empty(self, test_db):
+    def test_list_scans_empty(self, db):
         """Test listing scans when database is empty."""
-        service = ScanService(test_db)
+        service = ScanService(db)
 
         result = service.list_scans(page=1, per_page=20)
 
@@ -100,13 +93,13 @@ class TestScanServiceList:
         assert len(result.items) == 0
         assert result.pages == 0
 
-    def test_list_scans_with_data(self, test_db, sample_config_file):
+    def test_list_scans_with_data(self, db, sample_db_config):
         """Test listing scans with multiple scans."""
-        service = ScanService(test_db)
+        service = ScanService(db)
 
         # Create 3 scans
         for i in range(3):
-            service.trigger_scan(sample_config_file, triggered_by='api')
+            service.trigger_scan(config_id=sample_db_config.id, triggered_by='api')
 
         # List all scans
         result = service.list_scans(page=1, per_page=20)
@@ -115,13 +108,13 @@ class TestScanServiceList:
         assert len(result.items) == 3
         assert result.pages == 1
 
-    def test_list_scans_pagination(self, test_db, sample_config_file):
+    def test_list_scans_pagination(self, db, sample_db_config):
         """Test pagination."""
-        service = ScanService(test_db)
+        service = ScanService(db)
 
         # Create 5 scans
         for i in range(5):
-            service.trigger_scan(sample_config_file)
+            service.trigger_scan(config_id=sample_db_config.id)
 
         # Get page 1 (2 items per page)
         result = service.list_scans(page=1, per_page=2)
@@ -141,18 +134,18 @@ class TestScanServiceList:
         assert len(result.items) == 1
         assert result.has_next is False
 
-    def test_list_scans_filter_by_status(self, test_db, sample_config_file):
+    def test_list_scans_filter_by_status(self, db, sample_db_config):
         """Test filtering scans by status."""
-        service = ScanService(test_db)
+        service = ScanService(db)
 
         # Create scans with different statuses
-        scan_id_1 = service.trigger_scan(sample_config_file)
-        scan_id_2 = service.trigger_scan(sample_config_file)
+        scan_id_1 = service.trigger_scan(config_id=sample_db_config.id)
+        scan_id_2 = service.trigger_scan(config_id=sample_db_config.id)
 
         # Mark one as completed
-        scan = test_db.query(Scan).filter(Scan.id == scan_id_1).first()
+        scan = db.query(Scan).filter(Scan.id == scan_id_1).first()
         scan.status = 'completed'
-        test_db.commit()
+        db.commit()
 
         # Filter by running
         result = service.list_scans(status_filter='running')
@@ -162,9 +155,9 @@ class TestScanServiceList:
         result = service.list_scans(status_filter='completed')
         assert result.total == 1
 
-    def test_list_scans_invalid_status_filter(self, test_db):
+    def test_list_scans_invalid_status_filter(self, db):
         """Test filtering with invalid status."""
-        service = ScanService(test_db)
+        service = ScanService(db)
 
         with pytest.raises(ValueError, match="Invalid status"):
             service.list_scans(status_filter='invalid_status')
@@ -173,46 +166,46 @@ class TestScanServiceList:
 class TestScanServiceDelete:
     """Tests for deleting scans."""
 
-    def test_delete_scan_not_found(self, test_db):
+    def test_delete_scan_not_found(self, db):
         """Test deleting a nonexistent scan."""
-        service = ScanService(test_db)
+        service = ScanService(db)
 
         with pytest.raises(ValueError, match="not found"):
             service.delete_scan(999)
 
-    def test_delete_scan_success(self, test_db, sample_config_file):
+    def test_delete_scan_success(self, db, sample_db_config):
         """Test successful scan deletion."""
-        service = ScanService(test_db)
+        service = ScanService(db)
 
         # Create a scan
-        scan_id = service.trigger_scan(sample_config_file)
+        scan_id = service.trigger_scan(config_id=sample_db_config.id)
 
         # Verify it exists
-        assert test_db.query(Scan).filter(Scan.id == scan_id).first() is not None
+        assert db.query(Scan).filter(Scan.id == scan_id).first() is not None
 
         # Delete it
         result = service.delete_scan(scan_id)
         assert result is True
 
         # Verify it's gone
-        assert test_db.query(Scan).filter(Scan.id == scan_id).first() is None
+        assert db.query(Scan).filter(Scan.id == scan_id).first() is None
 
 
 class TestScanServiceStatus:
     """Tests for scan status retrieval."""
 
-    def test_get_scan_status_not_found(self, test_db):
+    def test_get_scan_status_not_found(self, db):
         """Test getting status of nonexistent scan."""
-        service = ScanService(test_db)
+        service = ScanService(db)
 
         result = service.get_scan_status(999)
         assert result is None
 
-    def test_get_scan_status_running(self, test_db, sample_config_file):
+    def test_get_scan_status_running(self, db, sample_db_config):
         """Test getting status of running scan."""
-        service = ScanService(test_db)
+        service = ScanService(db)
 
-        scan_id = service.trigger_scan(sample_config_file)
+        scan_id = service.trigger_scan(config_id=sample_db_config.id)
         status = service.get_scan_status(scan_id)
 
         assert status is not None
@@ -221,16 +214,16 @@ class TestScanServiceStatus:
         assert status['progress'] == 'In progress'
         assert status['title'] == 'Test Scan'
 
-    def test_get_scan_status_completed(self, test_db, sample_config_file):
+    def test_get_scan_status_completed(self, db, sample_db_config):
         """Test getting status of completed scan."""
-        service = ScanService(test_db)
+        service = ScanService(db)
 
         # Create and mark as completed
-        scan_id = service.trigger_scan(sample_config_file)
-        scan = test_db.query(Scan).filter(Scan.id == scan_id).first()
+        scan_id = service.trigger_scan(config_id=sample_db_config.id)
+        scan = db.query(Scan).filter(Scan.id == scan_id).first()
         scan.status = 'completed'
         scan.duration = 125.5
-        test_db.commit()
+        db.commit()
 
         status = service.get_scan_status(scan_id)
 
@@ -242,35 +235,35 @@ class TestScanServiceStatus:
 class TestScanServiceDatabaseMapping:
     """Tests for mapping scan reports to database models."""
 
-    def test_save_scan_to_db(self, test_db, sample_config_file, sample_scan_report):
+    def test_save_scan_to_db(self, db, sample_db_config, sample_scan_report):
         """Test saving a complete scan report to database."""
-        service = ScanService(test_db)
+        service = ScanService(db)
 
         # Create a scan
-        scan_id = service.trigger_scan(sample_config_file)
+        scan_id = service.trigger_scan(config_id=sample_db_config.id)
 
         # Save report to database
         service._save_scan_to_db(sample_scan_report, scan_id, status='completed')
 
         # Verify scan updated
-        scan = test_db.query(Scan).filter(Scan.id == scan_id).first()
+        scan = db.query(Scan).filter(Scan.id == scan_id).first()
         assert scan.status == 'completed'
         assert scan.duration == 125.5
 
         # Verify sites created
-        sites = test_db.query(ScanSite).filter(ScanSite.scan_id == scan_id).all()
+        sites = db.query(ScanSite).filter(ScanSite.scan_id == scan_id).all()
         assert len(sites) == 1
         assert sites[0].site_name == 'Test Site'
 
         # Verify IPs created
-        ips = test_db.query(ScanIP).filter(ScanIP.scan_id == scan_id).all()
+        ips = db.query(ScanIP).filter(ScanIP.scan_id == scan_id).all()
         assert len(ips) == 1
         assert ips[0].ip_address == '192.168.1.10'
         assert ips[0].ping_expected is True
         assert ips[0].ping_actual is True
 
         # Verify ports created (TCP: 22, 80, 443, 8080 | UDP: 53)
-        ports = test_db.query(ScanPort).filter(ScanPort.scan_id == scan_id).all()
+        ports = db.query(ScanPort).filter(ScanPort.scan_id == scan_id).all()
         assert len(ports) == 5  # 4 TCP + 1 UDP
 
         # Verify TCP ports
@@ -285,7 +278,7 @@ class TestScanServiceDatabaseMapping:
         assert udp_ports[0].port == 53
 
         # Verify services created
-        services = test_db.query(ScanServiceModel).filter(
+        services = db.query(ScanServiceModel).filter(
             ScanServiceModel.scan_id == scan_id
         ).all()
         assert len(services) == 4  # SSH, HTTP (80), HTTPS, HTTP (8080)
@@ -300,15 +293,15 @@ class TestScanServiceDatabaseMapping:
         assert https_service.http_protocol == 'https'
         assert https_service.screenshot_path == 'screenshots/192_168_1_10_443.png'
 
-    def test_map_port_expected_vs_actual(self, test_db, sample_config_file, sample_scan_report):
+    def test_map_port_expected_vs_actual(self, db, sample_db_config, sample_scan_report):
         """Test that expected vs actual ports are correctly flagged."""
-        service = ScanService(test_db)
+        service = ScanService(db)
 
-        scan_id = service.trigger_scan(sample_config_file)
+        scan_id = service.trigger_scan(config_id=sample_db_config.id)
         service._save_scan_to_db(sample_scan_report, scan_id)
 
         # Check TCP ports
-        tcp_ports = test_db.query(ScanPort).filter(
+        tcp_ports = db.query(ScanPort).filter(
             ScanPort.scan_id == scan_id,
             ScanPort.protocol == 'tcp'
         ).all()
@@ -322,15 +315,15 @@ class TestScanServiceDatabaseMapping:
                 # Port 8080 was not expected
                 assert port.expected is False, f"Port {port.port} should not be expected"
 
-    def test_map_certificate_and_tls(self, test_db, sample_config_file, sample_scan_report):
+    def test_map_certificate_and_tls(self, db, sample_db_config, sample_scan_report):
         """Test that certificate and TLS data are correctly mapped."""
-        service = ScanService(test_db)
+        service = ScanService(db)
 
-        scan_id = service.trigger_scan(sample_config_file)
+        scan_id = service.trigger_scan(config_id=sample_db_config.id)
         service._save_scan_to_db(sample_scan_report, scan_id)
 
         # Find HTTPS service
-        https_service = test_db.query(ScanServiceModel).filter(
+        https_service = db.query(ScanServiceModel).filter(
             ScanServiceModel.scan_id == scan_id,
             ScanServiceModel.service_name == 'https'
         ).first()
@@ -363,11 +356,11 @@ class TestScanServiceDatabaseMapping:
         assert tls_13 is not None
         assert tls_13.supported is True
 
-    def test_get_scan_with_full_details(self, test_db, sample_config_file, sample_scan_report):
+    def test_get_scan_with_full_details(self, db, sample_db_config, sample_scan_report):
         """Test retrieving scan with all nested relationships."""
-        service = ScanService(test_db)
+        service = ScanService(db)
 
-        scan_id = service.trigger_scan(sample_config_file)
+        scan_id = service.trigger_scan(config_id=sample_db_config.id)
         service._save_scan_to_db(sample_scan_report, scan_id)
 
         # Get full scan details

app/tests/test_schedule_api.py

@@ -13,20 +13,20 @@ from web.models import Schedule, Scan
 
 
 @pytest.fixture
-def sample_schedule(db, sample_config_file):
+def sample_schedule(db, sample_db_config):
     """
     Create a sample schedule in the database for testing.
 
     Args:
         db: Database session fixture
-        sample_config_file: Path to test config file
+        sample_db_config: Path to test config file
 
     Returns:
         Schedule model instance
     """
     schedule = Schedule(
         name='Daily Test Scan',
-        config_file=sample_config_file,
+        config_id=sample_db_config.id,
         cron_expression='0 2 * * *',
         enabled=True,
         last_run=None,
@@ -68,13 +68,13 @@ class TestScheduleAPIEndpoints:
         assert data['schedules'][0]['name'] == sample_schedule.name
         assert data['schedules'][0]['cron_expression'] == sample_schedule.cron_expression
 
-    def test_list_schedules_pagination(self, client, db, sample_config_file):
+    def test_list_schedules_pagination(self, client, db, sample_db_config):
         """Test schedule list pagination."""
         # Create 25 schedules
         for i in range(25):
             schedule = Schedule(
                 name=f'Schedule {i}',
-                config_file=sample_config_file,
+                config_id=sample_db_config.id,
                 cron_expression='0 2 * * *',
                 enabled=True,
                 created_at=datetime.utcnow()
@@ -101,13 +101,13 @@ class TestScheduleAPIEndpoints:
         assert len(data['schedules']) == 10
         assert data['page'] == 2
 
-    def test_list_schedules_filter_enabled(self, client, db, sample_config_file):
+    def test_list_schedules_filter_enabled(self, client, db, sample_db_config):
         """Test filtering schedules by enabled status."""
         # Create enabled and disabled schedules
         for i in range(3):
             schedule = Schedule(
                 name=f'Enabled Schedule {i}',
-                config_file=sample_config_file,
+                config_id=sample_db_config.id,
                 cron_expression='0 2 * * *',
                 enabled=True,
                 created_at=datetime.utcnow()
@@ -117,7 +117,7 @@ class TestScheduleAPIEndpoints:
         for i in range(2):
             schedule = Schedule(
                 name=f'Disabled Schedule {i}',
-                config_file=sample_config_file,
+                config_id=sample_db_config.id,
                 cron_expression='0 3 * * *',
                 enabled=False,
                 created_at=datetime.utcnow()
@@ -151,7 +151,7 @@ class TestScheduleAPIEndpoints:
         data = json.loads(response.data)
         assert data['id'] == sample_schedule.id
         assert data['name'] == sample_schedule.name
-        assert data['config_file'] == sample_schedule.config_file
+        assert data['config_id'] == sample_schedule.config_id
         assert data['cron_expression'] == sample_schedule.cron_expression
         assert data['enabled'] == sample_schedule.enabled
         assert 'history' in data
@@ -165,11 +165,11 @@ class TestScheduleAPIEndpoints:
         assert 'error' in data
         assert 'not found' in data['error'].lower()
 
-    def test_create_schedule(self, client, db, sample_config_file):
+    def test_create_schedule(self, client, db, sample_db_config):
         """Test creating a new schedule."""
         schedule_data = {
             'name': 'New Test Schedule',
-            'config_file': sample_config_file,
+            'config_id': sample_db_config.id,
             'cron_expression': '0 3 * * *',
             'enabled': True
         }
@@ -197,7 +197,7 @@ class TestScheduleAPIEndpoints:
         # Missing cron_expression
         schedule_data = {
             'name': 'Incomplete Schedule',
-            'config_file': '/app/configs/test.yaml'
+            'config_id': 1
         }
 
         response = client.post(
@@ -211,11 +211,11 @@ class TestScheduleAPIEndpoints:
         assert 'error' in data
         assert 'missing' in data['error'].lower()
 
-    def test_create_schedule_invalid_cron(self, client, db, sample_config_file):
+    def test_create_schedule_invalid_cron(self, client, db, sample_db_config):
         """Test creating schedule with invalid cron expression."""
         schedule_data = {
             'name': 'Invalid Cron Schedule',
-            'config_file': sample_config_file,
+            'config_id': sample_db_config.id,
             'cron_expression': 'invalid cron'
         }
 
@@ -231,10 +231,10 @@ class TestScheduleAPIEndpoints:
         assert 'invalid' in data['error'].lower() or 'cron' in data['error'].lower()
 
     def test_create_schedule_invalid_config(self, client, db):
-        """Test creating schedule with non-existent config file."""
+        """Test creating schedule with non-existent config."""
         schedule_data = {
             'name': 'Invalid Config Schedule',
-            'config_file': '/nonexistent/config.yaml',
+            'config_id': 99999,
             'cron_expression': '0 2 * * *'
         }
 
@@ -360,13 +360,13 @@ class TestScheduleAPIEndpoints:
         data = json.loads(response.data)
         assert 'error' in data
 
-    def test_delete_schedule_preserves_scans(self, client, db, sample_schedule, sample_config_file):
+    def test_delete_schedule_preserves_scans(self, client, db, sample_schedule, sample_db_config):
         """Test that deleting schedule preserves associated scans."""
         # Create a scan associated with the schedule
         scan = Scan(
             timestamp=datetime.utcnow(),
             status='completed',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             title='Test Scan',
             triggered_by='scheduled',
             schedule_id=sample_schedule.id
@@ -399,7 +399,7 @@ class TestScheduleAPIEndpoints:
         assert scan is not None
         assert scan.triggered_by == 'manual'
         assert scan.schedule_id == sample_schedule.id
-        assert scan.config_file == sample_schedule.config_file
+        assert scan.config_id == sample_schedule.config_id
 
     def test_trigger_schedule_not_found(self, client, db):
         """Test triggering non-existent schedule."""
@@ -409,14 +409,14 @@ class TestScheduleAPIEndpoints:
         data = json.loads(response.data)
         assert 'error' in data
 
-    def test_get_schedule_with_history(self, client, db, sample_schedule, sample_config_file):
+    def test_get_schedule_with_history(self, client, db, sample_schedule, sample_db_config):
         """Test getting schedule includes execution history."""
         # Create some scans for this schedule
         for i in range(5):
             scan = Scan(
                 timestamp=datetime.utcnow(),
                 status='completed',
-                config_file=sample_config_file,
+                config_id=sample_db_config.id,
                 title=f'Scheduled Scan {i}',
                 triggered_by='scheduled',
                 schedule_id=sample_schedule.id
@@ -431,12 +431,12 @@ class TestScheduleAPIEndpoints:
         assert 'history' in data
         assert len(data['history']) == 5
 
-    def test_schedule_workflow_integration(self, client, db, sample_config_file):
+    def test_schedule_workflow_integration(self, client, db, sample_db_config):
         """Test complete schedule workflow: create → update → trigger → delete."""
         # 1. Create schedule
         schedule_data = {
             'name': 'Integration Test Schedule',
-            'config_file': sample_config_file,
+            'config_id': sample_db_config.id,
             'cron_expression': '0 2 * * *',
             'enabled': True
         }
@@ -482,14 +482,14 @@ class TestScheduleAPIEndpoints:
         scan = db.query(Scan).filter(Scan.id == scan_id).first()
         assert scan is not None
 
-    def test_list_schedules_ordering(self, client, db, sample_config_file):
+    def test_list_schedules_ordering(self, client, db, sample_db_config):
         """Test that schedules are ordered by next_run time."""
         # Create schedules with different next_run times
         schedules = []
         for i in range(3):
             schedule = Schedule(
                 name=f'Schedule {i}',
-                config_file=sample_config_file,
+                config_id=sample_db_config.id,
                 cron_expression='0 2 * * *',
                 enabled=True,
                 next_run=datetime(2025, 11, 15 + i, 2, 0, 0),
@@ -501,7 +501,7 @@ class TestScheduleAPIEndpoints:
         # Create a disabled schedule (next_run is None)
         disabled_schedule = Schedule(
             name='Disabled Schedule',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 3 * * *',
             enabled=False,
             next_run=None,
@@ -523,11 +523,11 @@ class TestScheduleAPIEndpoints:
         assert returned_schedules[2]['id'] == schedules[2].id
         assert returned_schedules[3]['id'] == disabled_schedule.id
 
-    def test_create_schedule_with_disabled(self, client, db, sample_config_file):
+    def test_create_schedule_with_disabled(self, client, db, sample_db_config):
         """Test creating a disabled schedule."""
         schedule_data = {
             'name': 'Disabled Schedule',
-            'config_file': sample_config_file,
+            'config_id': sample_db_config.id,
             'cron_expression': '0 2 * * *',
             'enabled': False
         }
@@ -587,7 +587,7 @@ class TestScheduleAPIAuthentication:
 class TestScheduleAPICronValidation:
     """Test suite for cron expression validation."""
 
-    def test_valid_cron_expressions(self, client, db, sample_config_file):
+    def test_valid_cron_expressions(self, client, db, sample_db_config):
         """Test various valid cron expressions."""
         valid_expressions = [
             '0 2 * * *',      # Daily at 2am
@@ -600,7 +600,7 @@ class TestScheduleAPICronValidation:
         for cron_expr in valid_expressions:
             schedule_data = {
                 'name': f'Schedule for {cron_expr}',
-                'config_file': sample_config_file,
+                'config_id': sample_db_config.id,
                 'cron_expression': cron_expr
             }
 
@@ -612,7 +612,7 @@ class TestScheduleAPICronValidation:
             assert response.status_code == 201, \
                 f"Valid cron expression '{cron_expr}' should be accepted"
 
-    def test_invalid_cron_expressions(self, client, db, sample_config_file):
+    def test_invalid_cron_expressions(self, client, db, sample_db_config):
         """Test various invalid cron expressions."""
         invalid_expressions = [
             'invalid',
@@ -626,7 +626,7 @@ class TestScheduleAPICronValidation:
         for cron_expr in invalid_expressions:
             schedule_data = {
                 'name': f'Schedule for {cron_expr}',
-                'config_file': sample_config_file,
+                'config_id': sample_db_config.id,
                 'cron_expression': cron_expr
             }
 

app/tests/test_schedule_service.py

@@ -15,13 +15,13 @@ from web.services.schedule_service import ScheduleService
 class TestScheduleServiceCreate:
     """Tests for creating schedules."""
 
-    def test_create_schedule_valid(self, test_db, sample_config_file):
+    def test_create_schedule_valid(self, db, sample_db_config):
         """Test creating a schedule with valid parameters."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         schedule_id = service.create_schedule(
             name='Daily Scan',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 2 * * *',
             enabled=True
         )
@@ -31,57 +31,57 @@ class TestScheduleServiceCreate:
         assert isinstance(schedule_id, int)
 
         # Verify schedule in database
-        schedule = test_db.query(Schedule).filter(Schedule.id == schedule_id).first()
+        schedule = db.query(Schedule).filter(Schedule.id == schedule_id).first()
         assert schedule is not None
         assert schedule.name == 'Daily Scan'
-        assert schedule.config_file == sample_config_file
+        assert schedule.config_id == sample_db_config.id
         assert schedule.cron_expression == '0 2 * * *'
         assert schedule.enabled is True
         assert schedule.next_run is not None
         assert schedule.last_run is None
 
-    def test_create_schedule_disabled(self, test_db, sample_config_file):
+    def test_create_schedule_disabled(self, db, sample_db_config):
         """Test creating a disabled schedule."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         schedule_id = service.create_schedule(
             name='Disabled Scan',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 3 * * *',
             enabled=False
         )
 
-        schedule = test_db.query(Schedule).filter(Schedule.id == schedule_id).first()
+        schedule = db.query(Schedule).filter(Schedule.id == schedule_id).first()
         assert schedule.enabled is False
         assert schedule.next_run is None
 
-    def test_create_schedule_invalid_cron(self, test_db, sample_config_file):
+    def test_create_schedule_invalid_cron(self, db, sample_db_config):
         """Test creating a schedule with invalid cron expression."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         with pytest.raises(ValueError, match="Invalid cron expression"):
             service.create_schedule(
                 name='Invalid Schedule',
-                config_file=sample_config_file,
+                config_id=sample_db_config.id,
                 cron_expression='invalid cron',
                 enabled=True
             )
 
-    def test_create_schedule_nonexistent_config(self, test_db):
-        """Test creating a schedule with nonexistent config file."""
-        service = ScheduleService(test_db)
+    def test_create_schedule_nonexistent_config(self, db):
+        """Test creating a schedule with nonexistent config."""
+        service = ScheduleService(db)
 
-        with pytest.raises(ValueError, match="Config file not found"):
+        with pytest.raises(ValueError, match="not found"):
             service.create_schedule(
                 name='Bad Config',
-                config_file='/nonexistent/config.yaml',
+                config_id=99999,
                 cron_expression='0 2 * * *',
                 enabled=True
             )
 
-    def test_create_schedule_various_cron_expressions(self, test_db, sample_config_file):
+    def test_create_schedule_various_cron_expressions(self, db, sample_db_config):
         """Test creating schedules with various valid cron expressions."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         cron_expressions = [
             '0 0 * * *',      # Daily at midnight
@@ -94,7 +94,7 @@ class TestScheduleServiceCreate:
         for i, cron in enumerate(cron_expressions):
             schedule_id = service.create_schedule(
                 name=f'Schedule {i}',
-                config_file=sample_config_file,
+                config_id=sample_db_config.id,
                 cron_expression=cron,
                 enabled=True
             )
@@ -104,21 +104,21 @@ class TestScheduleServiceCreate:
 class TestScheduleServiceGet:
     """Tests for retrieving schedules."""
 
-    def test_get_schedule_not_found(self, test_db):
+    def test_get_schedule_not_found(self, db):
         """Test getting a nonexistent schedule."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         with pytest.raises(ValueError, match="Schedule .* not found"):
             service.get_schedule(999)
 
-    def test_get_schedule_found(self, test_db, sample_config_file):
+    def test_get_schedule_found(self, db, sample_db_config):
         """Test getting an existing schedule."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         # Create a schedule
         schedule_id = service.create_schedule(
             name='Test Schedule',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 2 * * *',
             enabled=True
         )
@@ -134,14 +134,14 @@ class TestScheduleServiceGet:
         assert 'history' in result
         assert isinstance(result['history'], list)
 
-    def test_get_schedule_with_history(self, test_db, sample_config_file):
+    def test_get_schedule_with_history(self, db, sample_db_config):
         """Test getting schedule includes execution history."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         # Create schedule
         schedule_id = service.create_schedule(
             name='Test Schedule',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 2 * * *',
             enabled=True
         )
@@ -151,13 +151,13 @@ class TestScheduleServiceGet:
             scan = Scan(
                 timestamp=datetime.utcnow() - timedelta(days=i),
                 status='completed',
-                config_file=sample_config_file,
+                config_id=sample_db_config.id,
                 title=f'Scan {i}',
                 triggered_by='scheduled',
                 schedule_id=schedule_id
             )
-            test_db.add(scan)
-        test_db.commit()
+            db.add(scan)
+        db.commit()
 
         # Get schedule
         result = service.get_schedule(schedule_id)
@@ -169,9 +169,9 @@ class TestScheduleServiceGet:
 class TestScheduleServiceList:
     """Tests for listing schedules."""
 
-    def test_list_schedules_empty(self, test_db):
+    def test_list_schedules_empty(self, db):
         """Test listing schedules when database is empty."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         result = service.list_schedules(page=1, per_page=20)
 
@@ -180,15 +180,15 @@ class TestScheduleServiceList:
         assert result['page'] == 1
         assert result['per_page'] == 20
 
-    def test_list_schedules_populated(self, test_db, sample_config_file):
+    def test_list_schedules_populated(self, db, sample_db_config):
         """Test listing schedules with data."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         # Create multiple schedules
         for i in range(5):
             service.create_schedule(
                 name=f'Schedule {i}',
-                config_file=sample_config_file,
+                config_id=sample_db_config.id,
                 cron_expression='0 2 * * *',
                 enabled=True
             )
@@ -199,15 +199,15 @@ class TestScheduleServiceList:
         assert len(result['schedules']) == 5
         assert all('name' in s for s in result['schedules'])
 
-    def test_list_schedules_pagination(self, test_db, sample_config_file):
+    def test_list_schedules_pagination(self, db, sample_db_config):
         """Test schedule pagination."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         # Create 25 schedules
         for i in range(25):
             service.create_schedule(
                 name=f'Schedule {i:02d}',
-                config_file=sample_config_file,
+                config_id=sample_db_config.id,
                 cron_expression='0 2 * * *',
                 enabled=True
             )
@@ -226,22 +226,22 @@ class TestScheduleServiceList:
         result_page3 = service.list_schedules(page=3, per_page=10)
         assert len(result_page3['schedules']) == 5
 
-    def test_list_schedules_filter_enabled(self, test_db, sample_config_file):
+    def test_list_schedules_filter_enabled(self, db, sample_db_config):
         """Test filtering schedules by enabled status."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         # Create enabled and disabled schedules
         for i in range(3):
             service.create_schedule(
                 name=f'Enabled {i}',
-                config_file=sample_config_file,
+                config_id=sample_db_config.id,
                 cron_expression='0 2 * * *',
                 enabled=True
             )
         for i in range(2):
             service.create_schedule(
                 name=f'Disabled {i}',
-                config_file=sample_config_file,
+                config_id=sample_db_config.id,
                 cron_expression='0 2 * * *',
                 enabled=False
             )
@@ -262,13 +262,13 @@ class TestScheduleServiceList:
 class TestScheduleServiceUpdate:
     """Tests for updating schedules."""
 
-    def test_update_schedule_name(self, test_db, sample_config_file):
+    def test_update_schedule_name(self, db, sample_db_config):
         """Test updating schedule name."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         schedule_id = service.create_schedule(
             name='Old Name',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 2 * * *',
             enabled=True
         )
@@ -278,13 +278,13 @@ class TestScheduleServiceUpdate:
         assert result['name'] == 'New Name'
         assert result['cron_expression'] == '0 2 * * *'
 
-    def test_update_schedule_cron(self, test_db, sample_config_file):
+    def test_update_schedule_cron(self, db, sample_db_config):
         """Test updating cron expression recalculates next_run."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         schedule_id = service.create_schedule(
             name='Test',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 2 * * *',
             enabled=True
         )
@@ -302,13 +302,13 @@ class TestScheduleServiceUpdate:
         assert result['cron_expression'] == '0 3 * * *'
         assert result['next_run'] != original_next_run
 
-    def test_update_schedule_invalid_cron(self, test_db, sample_config_file):
+    def test_update_schedule_invalid_cron(self, db, sample_db_config):
         """Test updating with invalid cron expression fails."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         schedule_id = service.create_schedule(
             name='Test',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 2 * * *',
             enabled=True
         )
@@ -316,67 +316,67 @@ class TestScheduleServiceUpdate:
         with pytest.raises(ValueError, match="Invalid cron expression"):
             service.update_schedule(schedule_id, cron_expression='invalid')
 
-    def test_update_schedule_not_found(self, test_db):
+    def test_update_schedule_not_found(self, db):
         """Test updating nonexistent schedule fails."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         with pytest.raises(ValueError, match="Schedule .* not found"):
             service.update_schedule(999, name='New Name')
 
-    def test_update_schedule_invalid_config_file(self, test_db, sample_config_file):
-        """Test updating with nonexistent config file fails."""
-        service = ScheduleService(test_db)
+    def test_update_schedule_invalid_config_id(self, db, sample_db_config):
+        """Test updating with nonexistent config ID fails."""
+        service = ScheduleService(db)
 
         schedule_id = service.create_schedule(
             name='Test',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 2 * * *',
             enabled=True
         )
 
-        with pytest.raises(ValueError, match="Config file not found"):
-            service.update_schedule(schedule_id, config_file='/nonexistent.yaml')
+        with pytest.raises(ValueError, match="not found"):
+            service.update_schedule(schedule_id, config_id=99999)
 
 
 class TestScheduleServiceDelete:
     """Tests for deleting schedules."""
 
-    def test_delete_schedule(self, test_db, sample_config_file):
+    def test_delete_schedule(self, db, sample_db_config):
         """Test deleting a schedule."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         schedule_id = service.create_schedule(
             name='To Delete',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 2 * * *',
             enabled=True
         )
 
         # Verify exists
-        assert test_db.query(Schedule).filter(Schedule.id == schedule_id).first() is not None
+        assert db.query(Schedule).filter(Schedule.id == schedule_id).first() is not None
 
         # Delete
         result = service.delete_schedule(schedule_id)
         assert result is True
 
         # Verify deleted
-        assert test_db.query(Schedule).filter(Schedule.id == schedule_id).first() is None
+        assert db.query(Schedule).filter(Schedule.id == schedule_id).first() is None
 
-    def test_delete_schedule_not_found(self, test_db):
+    def test_delete_schedule_not_found(self, db):
         """Test deleting nonexistent schedule fails."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         with pytest.raises(ValueError, match="Schedule .* not found"):
             service.delete_schedule(999)
 
-    def test_delete_schedule_preserves_scans(self, test_db, sample_config_file):
+    def test_delete_schedule_preserves_scans(self, db, sample_db_config):
         """Test that deleting schedule preserves associated scans."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         # Create schedule
         schedule_id = service.create_schedule(
             name='Test',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 2 * * *',
             enabled=True
         )
@@ -385,20 +385,20 @@ class TestScheduleServiceDelete:
         scan = Scan(
             timestamp=datetime.utcnow(),
             status='completed',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             title='Test Scan',
             triggered_by='scheduled',
             schedule_id=schedule_id
         )
-        test_db.add(scan)
-        test_db.commit()
+        db.add(scan)
+        db.commit()
         scan_id = scan.id
 
         # Delete schedule
         service.delete_schedule(schedule_id)
 
         # Verify scan still exists (schedule_id becomes null)
-        remaining_scan = test_db.query(Scan).filter(Scan.id == scan_id).first()
+        remaining_scan = db.query(Scan).filter(Scan.id == scan_id).first()
         assert remaining_scan is not None
         assert remaining_scan.schedule_id is None
 
@@ -406,13 +406,13 @@ class TestScheduleServiceDelete:
 class TestScheduleServiceToggle:
     """Tests for toggling schedule enabled status."""
 
-    def test_toggle_enabled_to_disabled(self, test_db, sample_config_file):
+    def test_toggle_enabled_to_disabled(self, db, sample_db_config):
         """Test disabling an enabled schedule."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         schedule_id = service.create_schedule(
             name='Test',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 2 * * *',
             enabled=True
         )
@@ -422,13 +422,13 @@ class TestScheduleServiceToggle:
         assert result['enabled'] is False
         assert result['next_run'] is None
 
-    def test_toggle_disabled_to_enabled(self, test_db, sample_config_file):
+    def test_toggle_disabled_to_enabled(self, db, sample_db_config):
         """Test enabling a disabled schedule."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         schedule_id = service.create_schedule(
             name='Test',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 2 * * *',
             enabled=False
         )
@@ -442,13 +442,13 @@ class TestScheduleServiceToggle:
 class TestScheduleServiceRunTimes:
     """Tests for updating run times."""
 
-    def test_update_run_times(self, test_db, sample_config_file):
+    def test_update_run_times(self, db, sample_db_config):
         """Test updating last_run and next_run."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         schedule_id = service.create_schedule(
             name='Test',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 2 * * *',
             enabled=True
         )
@@ -463,9 +463,9 @@ class TestScheduleServiceRunTimes:
         assert schedule['last_run'] is not None
         assert schedule['next_run'] is not None
 
-    def test_update_run_times_not_found(self, test_db):
+    def test_update_run_times_not_found(self, db):
         """Test updating run times for nonexistent schedule."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         with pytest.raises(ValueError, match="Schedule .* not found"):
             service.update_run_times(
@@ -478,9 +478,9 @@ class TestScheduleServiceRunTimes:
 class TestCronValidation:
     """Tests for cron expression validation."""
 
-    def test_validate_cron_valid_expressions(self, test_db):
+    def test_validate_cron_valid_expressions(self, db):
         """Test validating various valid cron expressions."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         valid_expressions = [
             '0 0 * * *',      # Daily at midnight
@@ -496,9 +496,9 @@ class TestCronValidation:
             assert is_valid is True, f"Expression '{expr}' should be valid"
             assert error is None
 
-    def test_validate_cron_invalid_expressions(self, test_db):
+    def test_validate_cron_invalid_expressions(self, db):
         """Test validating invalid cron expressions."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         invalid_expressions = [
             'invalid',
@@ -518,9 +518,9 @@ class TestCronValidation:
 class TestNextRunCalculation:
     """Tests for next run time calculation."""
 
-    def test_calculate_next_run(self, test_db):
+    def test_calculate_next_run(self, db):
         """Test calculating next run time."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         # Daily at 2 AM
         next_run = service.calculate_next_run('0 2 * * *')
@@ -529,9 +529,9 @@ class TestNextRunCalculation:
         assert isinstance(next_run, datetime)
         assert next_run > datetime.utcnow()
 
-    def test_calculate_next_run_from_time(self, test_db):
+    def test_calculate_next_run_from_time(self, db):
         """Test calculating next run from specific time."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         base_time = datetime(2025, 1, 1, 0, 0, 0)
         next_run = service.calculate_next_run('0 2 * * *', from_time=base_time)
@@ -540,9 +540,9 @@ class TestNextRunCalculation:
         assert next_run.hour == 2
         assert next_run.minute == 0
 
-    def test_calculate_next_run_invalid_cron(self, test_db):
+    def test_calculate_next_run_invalid_cron(self, db):
         """Test calculating next run with invalid cron raises error."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         with pytest.raises(ValueError, match="Invalid cron expression"):
             service.calculate_next_run('invalid cron')
@@ -551,13 +551,13 @@ class TestNextRunCalculation:
 class TestScheduleHistory:
     """Tests for schedule execution history."""
 
-    def test_get_schedule_history_empty(self, test_db, sample_config_file):
+    def test_get_schedule_history_empty(self, db, sample_db_config):
         """Test getting history for schedule with no executions."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         schedule_id = service.create_schedule(
             name='Test',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 2 * * *',
             enabled=True
         )
@@ -565,13 +565,13 @@ class TestScheduleHistory:
         history = service.get_schedule_history(schedule_id)
         assert len(history) == 0
 
-    def test_get_schedule_history_with_scans(self, test_db, sample_config_file):
+    def test_get_schedule_history_with_scans(self, db, sample_db_config):
         """Test getting history with multiple scans."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         schedule_id = service.create_schedule(
             name='Test',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 2 * * *',
             enabled=True
         )
@@ -581,26 +581,26 @@ class TestScheduleHistory:
             scan = Scan(
                 timestamp=datetime.utcnow() - timedelta(days=i),
                 status='completed',
-                config_file=sample_config_file,
+                config_id=sample_db_config.id,
                 title=f'Scan {i}',
                 triggered_by='scheduled',
                 schedule_id=schedule_id
             )
-            test_db.add(scan)
-        test_db.commit()
+            db.add(scan)
+        db.commit()
 
         # Get history (default limit 10)
         history = service.get_schedule_history(schedule_id, limit=10)
         assert len(history) == 10
         assert history[0]['title'] == 'Scan 0'  # Most recent first
 
-    def test_get_schedule_history_custom_limit(self, test_db, sample_config_file):
+    def test_get_schedule_history_custom_limit(self, db, sample_db_config):
         """Test getting history with custom limit."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         schedule_id = service.create_schedule(
             name='Test',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 2 * * *',
             enabled=True
         )
@@ -610,13 +610,13 @@ class TestScheduleHistory:
             scan = Scan(
                 timestamp=datetime.utcnow() - timedelta(days=i),
                 status='completed',
-                config_file=sample_config_file,
+                config_id=sample_db_config.id,
                 title=f'Scan {i}',
                 triggered_by='scheduled',
                 schedule_id=schedule_id
             )
-            test_db.add(scan)
-        test_db.commit()
+            db.add(scan)
+        db.commit()
 
         # Get only 5
         history = service.get_schedule_history(schedule_id, limit=5)
@@ -626,13 +626,13 @@ class TestScheduleHistory:
 class TestScheduleSerialization:
     """Tests for schedule serialization."""
 
-    def test_schedule_to_dict(self, test_db, sample_config_file):
+    def test_schedule_to_dict(self, db, sample_db_config):
         """Test converting schedule to dictionary."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         schedule_id = service.create_schedule(
             name='Test Schedule',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 2 * * *',
             enabled=True
         )
@@ -642,7 +642,7 @@ class TestScheduleSerialization:
         # Verify all required fields
         assert 'id' in result
         assert 'name' in result
-        assert 'config_file' in result
+        assert 'config_id' in result
         assert 'cron_expression' in result
         assert 'enabled' in result
         assert 'last_run' in result
@@ -652,13 +652,13 @@ class TestScheduleSerialization:
         assert 'updated_at' in result
         assert 'history' in result
 
-    def test_schedule_relative_time_formatting(self, test_db, sample_config_file):
+    def test_schedule_relative_time_formatting(self, db, sample_db_config):
         """Test relative time formatting in schedule dict."""
-        service = ScheduleService(test_db)
+        service = ScheduleService(db)
 
         schedule_id = service.create_schedule(
             name='Test',
-            config_file=sample_config_file,
+            config_id=sample_db_config.id,
             cron_expression='0 2 * * *',
             enabled=True
         )

app/tests/test_stats_api.py

@@ -20,7 +20,7 @@ class TestStatsAPI:
             scan_date = today - timedelta(days=i)
             for j in range(i + 1):  # Create 1, 2, 3, 4, 5 scans per day
                 scan = Scan(
-                    config_file='/app/configs/test.yaml',
+                    config_id=1,
                     timestamp=scan_date,
                     status='completed',
                     duration=10.5
@@ -56,7 +56,7 @@ class TestStatsAPI:
         today = datetime.utcnow()
         for i in range(10):
             scan = Scan(
-                config_file='/app/configs/test.yaml',
+                config_id=1,
                 timestamp=today - timedelta(days=i),
                 status='completed',
                 duration=10.5
@@ -105,7 +105,7 @@ class TestStatsAPI:
 
         # Create scan 5 days ago
         scan1 = Scan(
-            config_file='/app/configs/test.yaml',
+            config_id=1,
             timestamp=today - timedelta(days=5),
             status='completed',
             duration=10.5
@@ -114,7 +114,7 @@ class TestStatsAPI:
 
         # Create scan 10 days ago
         scan2 = Scan(
-            config_file='/app/configs/test.yaml',
+            config_id=1,
             timestamp=today - timedelta(days=10),
             status='completed',
             duration=10.5
@@ -148,7 +148,7 @@ class TestStatsAPI:
         # 5 completed scans
         for i in range(5):
             scan = Scan(
-                config_file='/app/configs/test.yaml',
+                config_id=1,
                 timestamp=today - timedelta(days=i),
                 status='completed',
                 duration=10.5
@@ -158,7 +158,7 @@ class TestStatsAPI:
         # 2 failed scans
         for i in range(2):
             scan = Scan(
-                config_file='/app/configs/test.yaml',
+                config_id=1,
                 timestamp=today - timedelta(days=i),
                 status='failed',
                 duration=5.0
@@ -167,7 +167,7 @@ class TestStatsAPI:
 
         # 1 running scan
         scan = Scan(
-            config_file='/app/configs/test.yaml',
+            config_id=1,
             timestamp=today,
             status='running',
             duration=None
@@ -217,7 +217,7 @@ class TestStatsAPI:
         # Create 3 scans today
         for i in range(3):
             scan = Scan(
-                config_file='/app/configs/test.yaml',
+                config_id=1,
                 timestamp=today,
                 status='completed',
                 duration=10.5
@@ -227,7 +227,7 @@ class TestStatsAPI:
         # Create 2 scans yesterday
         for i in range(2):
             scan = Scan(
-                config_file='/app/configs/test.yaml',
+                config_id=1,
                 timestamp=yesterday,
                 status='completed',
                 duration=10.5
@@ -250,7 +250,7 @@ class TestStatsAPI:
         # Create scans over the last 10 days
         for i in range(10):
             scan = Scan(
-                config_file='/app/configs/test.yaml',
+                config_id=1,
                 timestamp=today - timedelta(days=i),
                 status='completed',
                 duration=10.5
@@ -275,7 +275,7 @@ class TestStatsAPI:
         """Test scan trend returns dates in correct format."""
         # Create a scan
         scan = Scan(
-            config_file='/app/configs/test.yaml',
+            config_id=1,
             timestamp=datetime.utcnow(),
             status='completed',
             duration=10.5

app/web/api/alerts.py

@@ -0,0 +1,535 @@
+"""
+Alerts API blueprint.
+
+Handles endpoints for viewing alert history and managing alert rules.
+"""
+
+import json
+from datetime import datetime, timedelta, timezone
+from flask import Blueprint, jsonify, request, current_app
+
+from web.auth.decorators import api_auth_required
+from web.models import Alert, AlertRule, Scan
+from web.services.alert_service import AlertService
+
+bp = Blueprint('alerts', __name__)
+
+
+@bp.route('', methods=['GET'])
+@api_auth_required
+def list_alerts():
+    """
+    List recent alerts.
+
+    Query params:
+        page: Page number (default: 1)
+        per_page: Items per page (default: 20)
+        alert_type: Filter by alert type
+        severity: Filter by severity (info, warning, critical)
+        acknowledged: Filter by acknowledgment status (true/false)
+        scan_id: Filter by specific scan
+        start_date: Filter alerts after this date (ISO format)
+        end_date: Filter alerts before this date (ISO format)
+
+    Returns:
+        JSON response with alerts list
+    """
+    # Get query parameters
+    page = request.args.get('page', 1, type=int)
+    per_page = min(request.args.get('per_page', 20, type=int), 100)  # Max 100 items
+    alert_type = request.args.get('alert_type')
+    severity = request.args.get('severity')
+    acknowledged = request.args.get('acknowledged')
+    scan_id = request.args.get('scan_id', type=int)
+    start_date = request.args.get('start_date')
+    end_date = request.args.get('end_date')
+
+    # Build query
+    query = current_app.db_session.query(Alert)
+
+    # Apply filters
+    if alert_type:
+        query = query.filter(Alert.alert_type == alert_type)
+    if severity:
+        query = query.filter(Alert.severity == severity)
+    if acknowledged is not None:
+        ack_bool = acknowledged.lower() == 'true'
+        query = query.filter(Alert.acknowledged == ack_bool)
+    if scan_id:
+        query = query.filter(Alert.scan_id == scan_id)
+    if start_date:
+        try:
+            start_dt = datetime.fromisoformat(start_date.replace('Z', '+00:00'))
+            query = query.filter(Alert.created_at >= start_dt)
+        except ValueError:
+            pass  # Ignore invalid date format
+    if end_date:
+        try:
+            end_dt = datetime.fromisoformat(end_date.replace('Z', '+00:00'))
+            query = query.filter(Alert.created_at <= end_dt)
+        except ValueError:
+            pass  # Ignore invalid date format
+
+    # Order by severity and date
+    query = query.order_by(
+        Alert.severity.desc(),  # Critical first, then warning, then info
+        Alert.created_at.desc()  # Most recent first
+    )
+
+    # Paginate
+    total = query.count()
+    alerts = query.offset((page - 1) * per_page).limit(per_page).all()
+
+    # Format response
+    alerts_data = []
+    for alert in alerts:
+        # Get scan info
+        scan = current_app.db_session.query(Scan).filter(Scan.id == alert.scan_id).first()
+
+        alerts_data.append({
+            'id': alert.id,
+            'scan_id': alert.scan_id,
+            'scan_title': scan.title if scan else None,
+            'rule_id': alert.rule_id,
+            'alert_type': alert.alert_type,
+            'severity': alert.severity,
+            'message': alert.message,
+            'ip_address': alert.ip_address,
+            'port': alert.port,
+            'acknowledged': alert.acknowledged,
+            'acknowledged_at': alert.acknowledged_at.isoformat() if alert.acknowledged_at else None,
+            'acknowledged_by': alert.acknowledged_by,
+            'email_sent': alert.email_sent,
+            'email_sent_at': alert.email_sent_at.isoformat() if alert.email_sent_at else None,
+            'webhook_sent': alert.webhook_sent,
+            'webhook_sent_at': alert.webhook_sent_at.isoformat() if alert.webhook_sent_at else None,
+            'created_at': alert.created_at.isoformat()
+        })
+
+    return jsonify({
+        'alerts': alerts_data,
+        'total': total,
+        'page': page,
+        'per_page': per_page,
+        'pages': (total + per_page - 1) // per_page  # Ceiling division
+    })
+
+
+@bp.route('/<int:alert_id>/acknowledge', methods=['POST'])
+@api_auth_required
+def acknowledge_alert(alert_id):
+    """
+    Acknowledge an alert.
+
+    Args:
+        alert_id: Alert ID to acknowledge
+
+    Returns:
+        JSON response with acknowledgment status
+    """
+    # Get username from auth context or default to 'api'
+    acknowledged_by = request.json.get('acknowledged_by', 'api') if request.json else 'api'
+
+    alert_service = AlertService(current_app.db_session)
+    success = alert_service.acknowledge_alert(alert_id, acknowledged_by)
+
+    if success:
+        return jsonify({
+            'status': 'success',
+            'message': f'Alert {alert_id} acknowledged',
+            'acknowledged_by': acknowledged_by
+        })
+    else:
+        return jsonify({
+            'status': 'error',
+            'message': f'Failed to acknowledge alert {alert_id}'
+        }), 400
+
+
+@bp.route('/acknowledge-all', methods=['POST'])
+@api_auth_required
+def acknowledge_all_alerts():
+    """
+    Acknowledge all unacknowledged alerts.
+
+    Returns:
+        JSON response with count of acknowledged alerts
+    """
+    acknowledged_by = request.json.get('acknowledged_by', 'api') if request.json else 'api'
+
+    try:
+        # Get all unacknowledged alerts
+        unacked_alerts = current_app.db_session.query(Alert).filter(
+            Alert.acknowledged == False
+        ).all()
+
+        count = 0
+        for alert in unacked_alerts:
+            alert.acknowledged = True
+            alert.acknowledged_at = datetime.now(timezone.utc)
+            alert.acknowledged_by = acknowledged_by
+            count += 1
+
+        current_app.db_session.commit()
+
+        return jsonify({
+            'status': 'success',
+            'message': f'Acknowledged {count} alerts',
+            'count': count,
+            'acknowledged_by': acknowledged_by
+        })
+
+    except Exception as e:
+        current_app.db_session.rollback()
+        return jsonify({
+            'status': 'error',
+            'message': f'Failed to acknowledge alerts: {str(e)}'
+        }), 500
+
+
+@bp.route('/rules', methods=['GET'])
+@api_auth_required
+def list_alert_rules():
+    """
+    List all alert rules.
+
+    Returns:
+        JSON response with alert rules
+    """
+    rules = current_app.db_session.query(AlertRule).order_by(AlertRule.name, AlertRule.rule_type).all()
+
+    rules_data = []
+    for rule in rules:
+        rules_data.append({
+            'id': rule.id,
+            'name': rule.name,
+            'rule_type': rule.rule_type,
+            'enabled': rule.enabled,
+            'threshold': rule.threshold,
+            'email_enabled': rule.email_enabled,
+            'webhook_enabled': rule.webhook_enabled,
+            'severity': rule.severity,
+            'filter_conditions': json.loads(rule.filter_conditions) if rule.filter_conditions else None,
+            'config_id': rule.config_id,
+            'config_title': rule.config.title if rule.config else None,
+            'created_at': rule.created_at.isoformat(),
+            'updated_at': rule.updated_at.isoformat() if rule.updated_at else None
+        })
+
+    return jsonify({
+        'rules': rules_data,
+        'total': len(rules_data)
+    })
+
+
+@bp.route('/rules', methods=['POST'])
+@api_auth_required
+def create_alert_rule():
+    """
+    Create a new alert rule.
+
+    Request body:
+        name: User-friendly rule name
+        rule_type: Type of alert rule (unexpected_port, drift_detection, cert_expiry, weak_tls, ping_failed)
+        threshold: Threshold value (e.g., days for cert expiry, percentage for drift)
+        enabled: Whether rule is active (default: true)
+        email_enabled: Send email for this rule (default: false)
+        webhook_enabled: Send webhook for this rule (default: false)
+        severity: Alert severity (critical, warning, info)
+        filter_conditions: JSON object with filter conditions
+        config_id: Optional config ID to apply rule to
+
+    Returns:
+        JSON response with created rule
+    """
+    data = request.get_json() or {}
+
+    # Validate required fields
+    if not data.get('rule_type'):
+        return jsonify({
+            'status': 'error',
+            'message': 'rule_type is required'
+        }), 400
+
+    # Valid rule types
+    valid_rule_types = ['unexpected_port', 'drift_detection', 'cert_expiry', 'weak_tls', 'ping_failed']
+    if data['rule_type'] not in valid_rule_types:
+        return jsonify({
+            'status': 'error',
+            'message': f'Invalid rule_type. Must be one of: {", ".join(valid_rule_types)}'
+        }), 400
+
+    # Valid severities
+    valid_severities = ['critical', 'warning', 'info']
+    if data.get('severity') and data['severity'] not in valid_severities:
+        return jsonify({
+            'status': 'error',
+            'message': f'Invalid severity. Must be one of: {", ".join(valid_severities)}'
+        }), 400
+
+    try:
+        # Validate config_id if provided
+        config_id = data.get('config_id')
+        if config_id:
+            from web.models import ScanConfig
+            config = current_app.db_session.query(ScanConfig).filter_by(id=config_id).first()
+            if not config:
+                return jsonify({
+                    'status': 'error',
+                    'message': f'Config with ID {config_id} not found'
+                }), 400
+
+        # Create new rule
+        rule = AlertRule(
+            name=data.get('name', f"{data['rule_type']} rule"),
+            rule_type=data['rule_type'],
+            enabled=data.get('enabled', True),
+            threshold=data.get('threshold'),
+            email_enabled=data.get('email_enabled', False),
+            webhook_enabled=data.get('webhook_enabled', False),
+            severity=data.get('severity', 'warning'),
+            filter_conditions=json.dumps(data['filter_conditions']) if data.get('filter_conditions') else None,
+            config_id=config_id,
+            created_at=datetime.now(timezone.utc),
+            updated_at=datetime.now(timezone.utc)
+        )
+
+        current_app.db_session.add(rule)
+        current_app.db_session.commit()
+
+        return jsonify({
+            'status': 'success',
+            'message': 'Alert rule created successfully',
+            'rule': {
+                'id': rule.id,
+                'name': rule.name,
+                'rule_type': rule.rule_type,
+                'enabled': rule.enabled,
+                'threshold': rule.threshold,
+                'email_enabled': rule.email_enabled,
+                'webhook_enabled': rule.webhook_enabled,
+                'severity': rule.severity,
+                'filter_conditions': json.loads(rule.filter_conditions) if rule.filter_conditions else None,
+                'config_id': rule.config_id,
+                'config_title': rule.config.title if rule.config else None,
+                'created_at': rule.created_at.isoformat(),
+                'updated_at': rule.updated_at.isoformat()
+            }
+        }), 201
+
+    except Exception as e:
+        current_app.db_session.rollback()
+        return jsonify({
+            'status': 'error',
+            'message': f'Failed to create alert rule: {str(e)}'
+        }), 500
+
+
+@bp.route('/rules/<int:rule_id>', methods=['PUT'])
+@api_auth_required
+def update_alert_rule(rule_id):
+    """
+    Update an existing alert rule.
+
+    Args:
+        rule_id: Alert rule ID to update
+
+    Request body:
+        name: User-friendly rule name (optional)
+        threshold: Threshold value (optional)
+        enabled: Whether rule is active (optional)
+        email_enabled: Send email for this rule (optional)
+        webhook_enabled: Send webhook for this rule (optional)
+        severity: Alert severity (optional)
+        filter_conditions: JSON object with filter conditions (optional)
+        config_id: Config ID to apply rule to (optional)
+
+    Returns:
+        JSON response with update status
+    """
+    data = request.get_json() or {}
+
+    # Get existing rule
+    rule = current_app.db_session.query(AlertRule).filter(AlertRule.id == rule_id).first()
+    if not rule:
+        return jsonify({
+            'status': 'error',
+            'message': f'Alert rule {rule_id} not found'
+        }), 404
+
+    # Valid severities
+    valid_severities = ['critical', 'warning', 'info']
+    if data.get('severity') and data['severity'] not in valid_severities:
+        return jsonify({
+            'status': 'error',
+            'message': f'Invalid severity. Must be one of: {", ".join(valid_severities)}'
+        }), 400
+
+    try:
+        # Validate config_id if provided
+        if 'config_id' in data:
+            config_id = data['config_id']
+            if config_id:
+                from web.models import ScanConfig
+                config = current_app.db_session.query(ScanConfig).filter_by(id=config_id).first()
+                if not config:
+                    return jsonify({
+                        'status': 'error',
+                        'message': f'Config with ID {config_id} not found'
+                    }), 400
+
+        # Update fields if provided
+        if 'name' in data:
+            rule.name = data['name']
+        if 'threshold' in data:
+            rule.threshold = data['threshold']
+        if 'enabled' in data:
+            rule.enabled = data['enabled']
+        if 'email_enabled' in data:
+            rule.email_enabled = data['email_enabled']
+        if 'webhook_enabled' in data:
+            rule.webhook_enabled = data['webhook_enabled']
+        if 'severity' in data:
+            rule.severity = data['severity']
+        if 'filter_conditions' in data:
+            rule.filter_conditions = json.dumps(data['filter_conditions']) if data['filter_conditions'] else None
+        if 'config_id' in data:
+            rule.config_id = data['config_id']
+
+        rule.updated_at = datetime.now(timezone.utc)
+
+        current_app.db_session.commit()
+
+        return jsonify({
+            'status': 'success',
+            'message': 'Alert rule updated successfully',
+            'rule': {
+                'id': rule.id,
+                'name': rule.name,
+                'rule_type': rule.rule_type,
+                'enabled': rule.enabled,
+                'threshold': rule.threshold,
+                'email_enabled': rule.email_enabled,
+                'webhook_enabled': rule.webhook_enabled,
+                'severity': rule.severity,
+                'filter_conditions': json.loads(rule.filter_conditions) if rule.filter_conditions else None,
+                'config_id': rule.config_id,
+                'config_title': rule.config.title if rule.config else None,
+                'created_at': rule.created_at.isoformat(),
+                'updated_at': rule.updated_at.isoformat()
+            }
+        })
+
+    except Exception as e:
+        current_app.db_session.rollback()
+        return jsonify({
+            'status': 'error',
+            'message': f'Failed to update alert rule: {str(e)}'
+        }), 500
+
+
+@bp.route('/rules/<int:rule_id>', methods=['DELETE'])
+@api_auth_required
+def delete_alert_rule(rule_id):
+    """
+    Delete an alert rule.
+
+    Args:
+        rule_id: Alert rule ID to delete
+
+    Returns:
+        JSON response with deletion status
+    """
+    # Get existing rule
+    rule = current_app.db_session.query(AlertRule).filter(AlertRule.id == rule_id).first()
+    if not rule:
+        return jsonify({
+            'status': 'error',
+            'message': f'Alert rule {rule_id} not found'
+        }), 404
+
+    try:
+        # Delete the rule (cascade will delete related alerts)
+        current_app.db_session.delete(rule)
+        current_app.db_session.commit()
+
+        return jsonify({
+            'status': 'success',
+            'message': f'Alert rule {rule_id} deleted successfully'
+        })
+
+    except Exception as e:
+        current_app.db_session.rollback()
+        return jsonify({
+            'status': 'error',
+            'message': f'Failed to delete alert rule: {str(e)}'
+        }), 500
+
+
+@bp.route('/stats', methods=['GET'])
+@api_auth_required
+def alert_stats():
+    """
+    Get alert statistics.
+
+    Query params:
+        days: Number of days to look back (default: 7)
+
+    Returns:
+        JSON response with alert statistics
+    """
+    days = request.args.get('days', 7, type=int)
+    cutoff_date = datetime.now(timezone.utc) - timedelta(days=days)
+
+    # Get alerts in date range
+    alerts = current_app.db_session.query(Alert).filter(Alert.created_at >= cutoff_date).all()
+
+    # Calculate statistics
+    total_alerts = len(alerts)
+    alerts_by_severity = {'critical': 0, 'warning': 0, 'info': 0}
+    alerts_by_type = {}
+    unacknowledged_count = 0
+
+    for alert in alerts:
+        # Count by severity
+        if alert.severity in alerts_by_severity:
+            alerts_by_severity[alert.severity] += 1
+
+        # Count by type
+        if alert.alert_type not in alerts_by_type:
+            alerts_by_type[alert.alert_type] = 0
+        alerts_by_type[alert.alert_type] += 1
+
+        # Count unacknowledged
+        if not alert.acknowledged:
+            unacknowledged_count += 1
+
+    return jsonify({
+        'stats': {
+            'total_alerts': total_alerts,
+            'unacknowledged_count': unacknowledged_count,
+            'alerts_by_severity': alerts_by_severity,
+            'alerts_by_type': alerts_by_type,
+            'date_range': {
+                'start': cutoff_date.isoformat(),
+                'end': datetime.now(timezone.utc).isoformat(),
+                'days': days
+            }
+        }
+    })
+
+
+# Health check endpoint
+@bp.route('/health', methods=['GET'])
+def health_check():
+    """
+    Health check endpoint for monitoring.
+
+    Returns:
+        JSON response with API health status
+    """
+    return jsonify({
+        'status': 'healthy',
+        'api': 'alerts',
+        'version': '1.0.0-phase5'
+    })

app/web/api/configs.py

@@ -0,0 +1,461 @@
+"""
+Configs API blueprint.
+
+Handles endpoints for managing scan configurations stored in the database.
+Provides REST API for creating, updating, and deleting configs that reference sites.
+"""
+
+import logging
+from flask import Blueprint, jsonify, request, current_app
+
+from web.auth.decorators import api_auth_required
+from web.services.config_service import ConfigService
+
+bp = Blueprint('configs', __name__)
+logger = logging.getLogger(__name__)
+
+
+# ============================================================================
+# Database-based Config Endpoints (Primary)
+# ============================================================================
+
+@bp.route('', methods=['GET'])
+@api_auth_required
+def list_configs():
+    """
+    List all scan configurations from database.
+
+    Returns:
+        JSON response with list of configs:
+        {
+            "configs": [
+                {
+                    "id": 1,
+                    "title": "Production Scan",
+                    "description": "Weekly production scan",
+                    "site_count": 3,
+                    "sites": [
+                        {"id": 1, "name": "Production DC"},
+                        {"id": 2, "name": "DMZ"}
+                    ],
+                    "created_at": "2025-11-19T10:30:00Z",
+                    "updated_at": "2025-11-19T10:30:00Z"
+                }
+            ]
+        }
+    """
+    try:
+        config_service = ConfigService(db_session=current_app.db_session)
+        configs = config_service.list_configs_db()
+
+        logger.info(f"Listed {len(configs)} configs from database")
+
+        return jsonify({
+            'configs': configs
+        })
+
+    except Exception as e:
+        logger.error(f"Unexpected error listing configs: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('', methods=['POST'])
+@api_auth_required
+def create_config():
+    """
+    Create a new scan configuration in the database.
+
+    Request:
+        JSON with:
+        {
+            "title": "Production Scan",
+            "description": "Weekly production scan (optional)",
+            "site_ids": [1, 2, 3]
+        }
+
+    Returns:
+        JSON response with created config:
+        {
+            "success": true,
+            "config": {
+                "id": 1,
+                "title": "Production Scan",
+                "description": "...",
+                "site_count": 3,
+                "sites": [...],
+                "created_at": "2025-11-19T10:30:00Z",
+                "updated_at": "2025-11-19T10:30:00Z"
+            }
+        }
+
+    Error responses:
+        - 400: Validation error or missing fields
+        - 500: Internal server error
+    """
+    try:
+        data = request.get_json()
+
+        if not data:
+            return jsonify({
+                'error': 'Bad request',
+                'message': 'Request body must be JSON'
+            }), 400
+
+        # Validate required fields
+        if 'title' not in data:
+            return jsonify({
+                'error': 'Bad request',
+                'message': 'Missing required field: title'
+            }), 400
+
+        if 'site_ids' not in data:
+            return jsonify({
+                'error': 'Bad request',
+                'message': 'Missing required field: site_ids'
+            }), 400
+
+        title = data['title']
+        description = data.get('description', None)
+        site_ids = data['site_ids']
+
+        if not isinstance(site_ids, list):
+            return jsonify({
+                'error': 'Bad request',
+                'message': 'Field site_ids must be an array'
+            }), 400
+
+        # Create config
+        config_service = ConfigService(db_session=current_app.db_session)
+        config = config_service.create_config(title, description, site_ids)
+
+        logger.info(f"Created config: {config['title']} (ID: {config['id']})")
+
+        return jsonify({
+            'success': True,
+            'config': config
+        }), 201
+
+    except ValueError as e:
+        logger.warning(f"Config validation failed: {str(e)}")
+        return jsonify({
+            'error': 'Validation error',
+            'message': str(e)
+        }), 400
+
+    except Exception as e:
+        logger.error(f"Unexpected error creating config: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:config_id>', methods=['GET'])
+@api_auth_required
+def get_config(config_id: int):
+    """
+    Get a scan configuration by ID.
+
+    Args:
+        config_id: Configuration ID
+
+    Returns:
+        JSON response with config details:
+        {
+            "id": 1,
+            "title": "Production Scan",
+            "description": "...",
+            "site_count": 3,
+            "sites": [
+                {
+                    "id": 1,
+                    "name": "Production DC",
+                    "description": "...",
+                    "ip_count": 5
+                }
+            ],
+            "created_at": "2025-11-19T10:30:00Z",
+            "updated_at": "2025-11-19T10:30:00Z"
+        }
+
+    Error responses:
+        - 404: Config not found
+        - 500: Internal server error
+    """
+    try:
+        config_service = ConfigService(db_session=current_app.db_session)
+        config = config_service.get_config_by_id(config_id)
+
+        logger.info(f"Retrieved config: {config['title']} (ID: {config_id})")
+
+        return jsonify(config)
+
+    except ValueError as e:
+        logger.warning(f"Config not found: {config_id}")
+        return jsonify({
+            'error': 'Not found',
+            'message': str(e)
+        }), 404
+
+    except Exception as e:
+        logger.error(f"Unexpected error getting config {config_id}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:config_id>', methods=['PUT'])
+@api_auth_required
+def update_config(config_id: int):
+    """
+    Update an existing scan configuration.
+
+    Args:
+        config_id: Configuration ID
+
+    Request:
+        JSON with (all fields optional):
+        {
+            "title": "New Title",
+            "description": "New Description",
+            "site_ids": [1, 2, 3]
+        }
+
+    Returns:
+        JSON response with updated config:
+        {
+            "success": true,
+            "config": {...}
+        }
+
+    Error responses:
+        - 400: Validation error
+        - 404: Config not found
+        - 500: Internal server error
+    """
+    try:
+        data = request.get_json()
+
+        if not data:
+            return jsonify({
+                'error': 'Bad request',
+                'message': 'Request body must be JSON'
+            }), 400
+
+        title = data.get('title', None)
+        description = data.get('description', None)
+        site_ids = data.get('site_ids', None)
+
+        if site_ids is not None and not isinstance(site_ids, list):
+            return jsonify({
+                'error': 'Bad request',
+                'message': 'Field site_ids must be an array'
+            }), 400
+
+        # Update config
+        config_service = ConfigService(db_session=current_app.db_session)
+        config = config_service.update_config(config_id, title, description, site_ids)
+
+        logger.info(f"Updated config: {config['title']} (ID: {config_id})")
+
+        return jsonify({
+            'success': True,
+            'config': config
+        })
+
+    except ValueError as e:
+        if 'not found' in str(e).lower():
+            logger.warning(f"Config not found: {config_id}")
+            return jsonify({
+                'error': 'Not found',
+                'message': str(e)
+            }), 404
+        else:
+            logger.warning(f"Config validation failed: {str(e)}")
+            return jsonify({
+                'error': 'Validation error',
+                'message': str(e)
+            }), 400
+
+    except Exception as e:
+        logger.error(f"Unexpected error updating config {config_id}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:config_id>', methods=['DELETE'])
+@api_auth_required
+def delete_config(config_id: int):
+    """
+    Delete a scan configuration.
+
+    Args:
+        config_id: Configuration ID
+
+    Returns:
+        JSON response with success status:
+        {
+            "success": true,
+            "message": "Config deleted successfully"
+        }
+
+    Error responses:
+        - 404: Config not found
+        - 500: Internal server error
+    """
+    try:
+        config_service = ConfigService(db_session=current_app.db_session)
+        config_service.delete_config(config_id)
+
+        logger.info(f"Deleted config (ID: {config_id})")
+
+        return jsonify({
+            'success': True,
+            'message': 'Config deleted successfully'
+        })
+
+    except ValueError as e:
+        logger.warning(f"Config not found: {config_id}")
+        return jsonify({
+            'error': 'Not found',
+            'message': str(e)
+        }), 404
+
+    except Exception as e:
+        logger.error(f"Unexpected error deleting config {config_id}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:config_id>/sites', methods=['POST'])
+@api_auth_required
+def add_site_to_config(config_id: int):
+    """
+    Add a site to an existing config.
+
+    Args:
+        config_id: Configuration ID
+
+    Request:
+        JSON with:
+        {
+            "site_id": 5
+        }
+
+    Returns:
+        JSON response with updated config:
+        {
+            "success": true,
+            "config": {...}
+        }
+
+    Error responses:
+        - 400: Validation error or site already in config
+        - 404: Config or site not found
+        - 500: Internal server error
+    """
+    try:
+        data = request.get_json()
+
+        if not data or 'site_id' not in data:
+            return jsonify({
+                'error': 'Bad request',
+                'message': 'Missing required field: site_id'
+            }), 400
+
+        site_id = data['site_id']
+
+        # Add site to config
+        config_service = ConfigService(db_session=current_app.db_session)
+        config = config_service.add_site_to_config(config_id, site_id)
+
+        logger.info(f"Added site {site_id} to config {config_id}")
+
+        return jsonify({
+            'success': True,
+            'config': config
+        })
+
+    except ValueError as e:
+        if 'not found' in str(e).lower():
+            logger.warning(f"Config or site not found: {str(e)}")
+            return jsonify({
+                'error': 'Not found',
+                'message': str(e)
+            }), 404
+        else:
+            logger.warning(f"Validation error: {str(e)}")
+            return jsonify({
+                'error': 'Validation error',
+                'message': str(e)
+            }), 400
+
+    except Exception as e:
+        logger.error(f"Unexpected error adding site to config: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:config_id>/sites/<int:site_id>', methods=['DELETE'])
+@api_auth_required
+def remove_site_from_config(config_id: int, site_id: int):
+    """
+    Remove a site from a config.
+
+    Args:
+        config_id: Configuration ID
+        site_id: Site ID to remove
+
+    Returns:
+        JSON response with updated config:
+        {
+            "success": true,
+            "config": {...}
+        }
+
+    Error responses:
+        - 400: Validation error (e.g., last site cannot be removed)
+        - 404: Config not found or site not in config
+        - 500: Internal server error
+    """
+    try:
+        config_service = ConfigService(db_session=current_app.db_session)
+        config = config_service.remove_site_from_config(config_id, site_id)
+
+        logger.info(f"Removed site {site_id} from config {config_id}")
+
+        return jsonify({
+            'success': True,
+            'config': config
+        })
+
+    except ValueError as e:
+        if 'not found' in str(e).lower() or 'not in this config' in str(e).lower():
+            logger.warning(f"Config or site not found: {str(e)}")
+            return jsonify({
+                'error': 'Not found',
+                'message': str(e)
+            }), 404
+        else:
+            logger.warning(f"Validation error: {str(e)}")
+            return jsonify({
+                'error': 'Validation error',
+                'message': str(e)
+            }), 400
+
+    except Exception as e:
+        logger.error(f"Unexpected error removing site from config: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500

app/web/api/scans.py

@@ -0,0 +1,642 @@
+"""
+Scans API blueprint.
+
+Handles endpoints for triggering scans, listing scan history, and retrieving
+scan results.
+"""
+
+import json
+import logging
+from datetime import datetime
+from pathlib import Path
+
+from flask import Blueprint, current_app, jsonify, request
+from sqlalchemy.exc import SQLAlchemyError
+
+from web.auth.decorators import api_auth_required
+from web.models import Scan, ScanProgress
+from web.services.scan_service import ScanService
+from web.utils.pagination import validate_page_params
+from web.jobs.scan_job import stop_scan
+
+bp = Blueprint('scans', __name__)
+logger = logging.getLogger(__name__)
+
+
+def _recover_orphaned_scan(scan: Scan, session) -> dict:
+    """
+    Recover an orphaned scan by checking for output files.
+
+    If output files exist: mark as 'completed' (smart recovery)
+    If no output files: mark as 'cancelled'
+
+    Args:
+        scan: The orphaned Scan object
+        session: Database session
+
+    Returns:
+        Dictionary with recovery result for API response
+    """
+    # Check for existing output files
+    output_exists = False
+    output_files_found = []
+
+    # Check paths stored in database
+    if scan.json_path and Path(scan.json_path).exists():
+        output_exists = True
+        output_files_found.append('json')
+    if scan.html_path and Path(scan.html_path).exists():
+        output_files_found.append('html')
+    if scan.zip_path and Path(scan.zip_path).exists():
+        output_files_found.append('zip')
+
+    # Also check by timestamp pattern if paths not stored yet
+    if not output_exists and scan.started_at:
+        output_dir = Path('/app/output')
+        if output_dir.exists():
+            timestamp_pattern = scan.started_at.strftime('%Y%m%d')
+            for json_file in output_dir.glob(f'scan_report_{timestamp_pattern}*.json'):
+                output_exists = True
+                output_files_found.append('json')
+                # Update scan record with found paths
+                scan.json_path = str(json_file)
+                html_file = json_file.with_suffix('.html')
+                if html_file.exists():
+                    scan.html_path = str(html_file)
+                    output_files_found.append('html')
+                zip_file = json_file.with_suffix('.zip')
+                if zip_file.exists():
+                    scan.zip_path = str(zip_file)
+                    output_files_found.append('zip')
+                break
+
+    if output_exists:
+        # Smart recovery: outputs exist, mark as completed
+        scan.status = 'completed'
+        scan.completed_at = datetime.utcnow()
+        if scan.started_at:
+            scan.duration = (datetime.utcnow() - scan.started_at).total_seconds()
+        scan.error_message = None
+        session.commit()
+
+        logger.info(f"Scan {scan.id}: Recovered as completed (files: {output_files_found})")
+
+        return {
+            'scan_id': scan.id,
+            'status': 'completed',
+            'message': f'Scan recovered as completed (output files found: {", ".join(output_files_found)})',
+            'recovery_type': 'smart_recovery'
+        }
+    else:
+        # No outputs: mark as cancelled
+        scan.status = 'cancelled'
+        scan.completed_at = datetime.utcnow()
+        if scan.started_at:
+            scan.duration = (datetime.utcnow() - scan.started_at).total_seconds()
+        scan.error_message = 'Scan process was interrupted before completion. No output files were generated.'
+        session.commit()
+
+        logger.info(f"Scan {scan.id}: Marked as cancelled (orphaned, no output files)")
+
+        return {
+            'scan_id': scan.id,
+            'status': 'cancelled',
+            'message': 'Orphaned scan cancelled (no output files found)',
+            'recovery_type': 'orphan_cleanup'
+        }
+
+
+@bp.route('', methods=['GET'])
+@api_auth_required
+def list_scans():
+    """
+    List all scans with pagination.
+
+    Query params:
+        page: Page number (default: 1)
+        per_page: Items per page (default: 20, max: 100)
+        status: Filter by status (running, completed, failed)
+
+    Returns:
+        JSON response with scans list and pagination info
+    """
+    try:
+        # Get and validate query parameters
+        page = request.args.get('page', 1, type=int)
+        per_page = request.args.get('per_page', 20, type=int)
+        status_filter = request.args.get('status', None, type=str)
+
+        # Validate pagination params
+        page, per_page = validate_page_params(page, per_page)
+
+        # Get scans from service
+        scan_service = ScanService(current_app.db_session)
+        paginated_result = scan_service.list_scans(
+            page=page,
+            per_page=per_page,
+            status_filter=status_filter
+        )
+
+        logger.info(f"Listed scans: page={page}, per_page={per_page}, status={status_filter}, total={paginated_result.total}")
+
+        return jsonify({
+            'scans': paginated_result.items,
+            'total': paginated_result.total,
+            'page': paginated_result.page,
+            'per_page': paginated_result.per_page,
+            'total_pages': paginated_result.pages,
+            'has_prev': paginated_result.has_prev,
+            'has_next': paginated_result.has_next
+        })
+
+    except ValueError as e:
+        logger.warning(f"Invalid request parameters: {str(e)}")
+        return jsonify({
+            'error': 'Invalid request',
+            'message': str(e)
+        }), 400
+    except SQLAlchemyError as e:
+        logger.error(f"Database error listing scans: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to retrieve scans'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error listing scans: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:scan_id>', methods=['GET'])
+@api_auth_required
+def get_scan(scan_id):
+    """
+    Get details for a specific scan.
+
+    Args:
+        scan_id: Scan ID
+
+    Returns:
+        JSON response with scan details
+    """
+    try:
+        # Get scan from service
+        scan_service = ScanService(current_app.db_session)
+        scan = scan_service.get_scan(scan_id)
+
+        if not scan:
+            logger.warning(f"Scan not found: {scan_id}")
+            return jsonify({
+                'error': 'Not found',
+                'message': f'Scan with ID {scan_id} not found'
+            }), 404
+
+        logger.info(f"Retrieved scan details: {scan_id}")
+        return jsonify(scan)
+
+    except SQLAlchemyError as e:
+        logger.error(f"Database error retrieving scan {scan_id}: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to retrieve scan'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error retrieving scan {scan_id}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('', methods=['POST'])
+@api_auth_required
+def trigger_scan():
+    """
+    Trigger a new scan.
+
+    Request body:
+        config_id: Database config ID (required)
+
+    Returns:
+        JSON response with scan_id and status
+    """
+    try:
+        # Get request data
+        data = request.get_json() or {}
+        config_id = data.get('config_id')
+
+        # Validate required fields
+        if not config_id:
+            logger.warning("Scan trigger request missing config_id")
+            return jsonify({
+                'error': 'Invalid request',
+                'message': 'config_id is required'
+            }), 400
+
+        # Validate config_id is an integer
+        try:
+            config_id = int(config_id)
+        except (TypeError, ValueError):
+            logger.warning(f"Invalid config_id type: {config_id}")
+            return jsonify({
+                'error': 'Invalid request',
+                'message': 'config_id must be an integer'
+            }), 400
+
+        # Trigger scan via service
+        scan_service = ScanService(current_app.db_session)
+        scan_id = scan_service.trigger_scan(
+            config_id=config_id,
+            triggered_by='api',
+            scheduler=current_app.scheduler
+        )
+
+        logger.info(f"Scan {scan_id} triggered via API: config_id={config_id}")
+
+        return jsonify({
+            'scan_id': scan_id,
+            'status': 'running',
+            'message': 'Scan queued successfully'
+        }), 201
+
+    except ValueError as e:
+        # Config validation error
+        error_message = str(e)
+        logger.warning(f"Invalid config: {error_message}")
+        logger.warning(f"Request data: config_id='{config_id}'")
+        return jsonify({
+            'error': 'Invalid request',
+            'message': error_message
+        }), 400
+    except SQLAlchemyError as e:
+        logger.error(f"Database error triggering scan: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to create scan'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error triggering scan: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:scan_id>', methods=['DELETE'])
+@api_auth_required
+def delete_scan(scan_id):
+    """
+    Delete a scan and its associated files.
+
+    Args:
+        scan_id: Scan ID to delete
+
+    Returns:
+        JSON response with deletion status
+    """
+    try:
+        # Delete scan via service
+        scan_service = ScanService(current_app.db_session)
+        scan_service.delete_scan(scan_id)
+
+        logger.info(f"Scan {scan_id} deleted successfully")
+
+        return jsonify({
+            'scan_id': scan_id,
+            'message': 'Scan deleted successfully'
+        }), 200
+
+    except ValueError as e:
+        # Scan not found
+        logger.warning(f"Scan deletion failed: {str(e)}")
+        return jsonify({
+            'error': 'Not found',
+            'message': str(e)
+        }), 404
+    except SQLAlchemyError as e:
+        logger.error(f"Database error deleting scan {scan_id}: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to delete scan'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error deleting scan {scan_id}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:scan_id>/stop', methods=['POST'])
+@api_auth_required
+def stop_running_scan(scan_id):
+    """
+    Stop a running scan with smart recovery for orphaned scans.
+
+    If the scan is actively running in the registry, sends a cancel signal.
+    If the scan shows as running/finalizing but is not in the registry (orphaned),
+    performs smart recovery: marks as 'completed' if output files exist,
+    otherwise marks as 'cancelled'.
+
+    Args:
+        scan_id: Scan ID to stop
+
+    Returns:
+        JSON response with stop status or recovery result
+    """
+    try:
+        session = current_app.db_session
+
+        # Check if scan exists
+        scan = session.query(Scan).filter_by(id=scan_id).first()
+        if not scan:
+            logger.warning(f"Scan not found for stop request: {scan_id}")
+            return jsonify({
+                'error': 'Not found',
+                'message': f'Scan with ID {scan_id} not found'
+            }), 404
+
+        # Allow stopping scans with status 'running' or 'finalizing'
+        if scan.status not in ('running', 'finalizing'):
+            logger.warning(f"Cannot stop scan {scan_id}: status is '{scan.status}'")
+            return jsonify({
+                'error': 'Invalid state',
+                'message': f"Cannot stop scan: status is '{scan.status}'"
+            }), 400
+
+        # Get database URL from app config
+        db_url = current_app.config['SQLALCHEMY_DATABASE_URI']
+
+        # Attempt to stop the scan
+        stopped = stop_scan(scan_id, db_url)
+
+        if stopped:
+            logger.info(f"Stop signal sent to scan {scan_id}")
+            return jsonify({
+                'scan_id': scan_id,
+                'message': 'Stop signal sent to scan',
+                'status': 'stopping'
+            }), 200
+        else:
+            # Scanner not in registry - this is an orphaned scan
+            # Attempt smart recovery
+            logger.warning(f"Scan {scan_id} not in registry, attempting smart recovery")
+            recovery_result = _recover_orphaned_scan(scan, session)
+            return jsonify(recovery_result), 200
+
+    except SQLAlchemyError as e:
+        logger.error(f"Database error stopping scan {scan_id}: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to stop scan'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error stopping scan {scan_id}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:scan_id>/status', methods=['GET'])
+@api_auth_required
+def get_scan_status(scan_id):
+    """
+    Get current status of a running scan.
+
+    Args:
+        scan_id: Scan ID
+
+    Returns:
+        JSON response with scan status and progress
+    """
+    try:
+        # Get scan status from service
+        scan_service = ScanService(current_app.db_session)
+        status = scan_service.get_scan_status(scan_id)
+
+        if not status:
+            logger.warning(f"Scan not found for status check: {scan_id}")
+            return jsonify({
+                'error': 'Not found',
+                'message': f'Scan with ID {scan_id} not found'
+            }), 404
+
+        logger.debug(f"Retrieved status for scan {scan_id}: {status['status']}")
+        return jsonify(status)
+
+    except SQLAlchemyError as e:
+        logger.error(f"Database error retrieving scan status {scan_id}: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to retrieve scan status'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error retrieving scan status {scan_id}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:scan_id>/progress', methods=['GET'])
+@api_auth_required
+def get_scan_progress(scan_id):
+    """
+    Get detailed progress for a running scan including per-IP results.
+
+    Args:
+        scan_id: Scan ID
+
+    Returns:
+        JSON response with scan progress including:
+        - current_phase: Current scan phase
+        - total_ips: Total IPs being scanned
+        - completed_ips: Number of IPs completed in current phase
+        - progress_entries: List of per-IP progress with discovered results
+    """
+    try:
+        session = current_app.db_session
+
+        # Get scan record
+        scan = session.query(Scan).filter_by(id=scan_id).first()
+        if not scan:
+            logger.warning(f"Scan not found for progress check: {scan_id}")
+            return jsonify({
+                'error': 'Not found',
+                'message': f'Scan with ID {scan_id} not found'
+            }), 404
+
+        # Get progress entries
+        progress_entries = session.query(ScanProgress).filter_by(scan_id=scan_id).all()
+
+        # Build progress data
+        entries = []
+        for entry in progress_entries:
+            entry_data = {
+                'ip_address': entry.ip_address,
+                'site_name': entry.site_name,
+                'phase': entry.phase,
+                'status': entry.status,
+                'ping_result': entry.ping_result
+            }
+
+            # Parse JSON fields
+            if entry.tcp_ports:
+                entry_data['tcp_ports'] = json.loads(entry.tcp_ports)
+            else:
+                entry_data['tcp_ports'] = []
+
+            if entry.udp_ports:
+                entry_data['udp_ports'] = json.loads(entry.udp_ports)
+            else:
+                entry_data['udp_ports'] = []
+
+            if entry.services:
+                entry_data['services'] = json.loads(entry.services)
+            else:
+                entry_data['services'] = []
+
+            entries.append(entry_data)
+
+        # Sort entries by site name then IP (numerically)
+        def ip_sort_key(ip_str):
+            """Convert IP to tuple of integers for proper numeric sorting."""
+            try:
+                return tuple(int(octet) for octet in ip_str.split('.'))
+            except (ValueError, AttributeError):
+                return (0, 0, 0, 0)
+
+        entries.sort(key=lambda x: (x['site_name'] or '', ip_sort_key(x['ip_address'])))
+
+        response = {
+            'scan_id': scan_id,
+            'status': scan.status,
+            'current_phase': scan.current_phase or 'pending',
+            'total_ips': scan.total_ips or 0,
+            'completed_ips': scan.completed_ips or 0,
+            'progress_entries': entries
+        }
+
+        logger.debug(f"Retrieved progress for scan {scan_id}: phase={scan.current_phase}, {scan.completed_ips}/{scan.total_ips} IPs")
+        return jsonify(response)
+
+    except SQLAlchemyError as e:
+        logger.error(f"Database error retrieving scan progress {scan_id}: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to retrieve scan progress'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error retrieving scan progress {scan_id}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/by-ip/<ip_address>', methods=['GET'])
+@api_auth_required
+def get_scans_by_ip(ip_address):
+    """
+    Get last 10 scans containing a specific IP address.
+
+    Args:
+        ip_address: IP address to search for
+
+    Returns:
+        JSON response with list of scans containing the IP
+    """
+    try:
+        # Get scans from service
+        scan_service = ScanService(current_app.db_session)
+        scans = scan_service.get_scans_by_ip(ip_address)
+
+        logger.info(f"Retrieved {len(scans)} scans for IP: {ip_address}")
+
+        return jsonify({
+            'ip_address': ip_address,
+            'scans': scans,
+            'count': len(scans)
+        })
+
+    except SQLAlchemyError as e:
+        logger.error(f"Database error retrieving scans for IP {ip_address}: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to retrieve scans'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error retrieving scans for IP {ip_address}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:scan_id1>/compare/<int:scan_id2>', methods=['GET'])
+@api_auth_required
+def compare_scans(scan_id1, scan_id2):
+    """
+    Compare two scans and show differences.
+
+    Compares ports, services, and certificates between two scans,
+    highlighting added, removed, and changed items.
+
+    Args:
+        scan_id1: First (older) scan ID
+        scan_id2: Second (newer) scan ID
+
+    Returns:
+        JSON response with comparison results including:
+        - scan1, scan2: Metadata for both scans
+        - ports: Added, removed, and unchanged ports
+        - services: Added, removed, and changed services
+        - certificates: Added, removed, and changed certificates
+        - drift_score: Overall drift metric (0.0-1.0)
+    """
+    try:
+        # Compare scans using service
+        scan_service = ScanService(current_app.db_session)
+        comparison = scan_service.compare_scans(scan_id1, scan_id2)
+
+        if not comparison:
+            logger.warning(f"Scan comparison failed: one or both scans not found ({scan_id1}, {scan_id2})")
+            return jsonify({
+                'error': 'Not found',
+                'message': 'One or both scans not found'
+            }), 404
+
+        logger.info(f"Compared scans {scan_id1} and {scan_id2}: drift_score={comparison['drift_score']}")
+        return jsonify(comparison), 200
+
+    except SQLAlchemyError as e:
+        logger.error(f"Database error comparing scans {scan_id1} and {scan_id2}: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to compare scans'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error comparing scans {scan_id1} and {scan_id2}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+# Health check endpoint
+@bp.route('/health', methods=['GET'])
+def health_check():
+    """
+    Health check endpoint for monitoring.
+
+    Returns:
+        JSON response with API health status
+    """
+    return jsonify({
+        'status': 'healthy',
+        'api': 'scans',
+        'version': '1.0.0-phase1'
+    })

app/web/api/schedules.py

@@ -88,7 +88,7 @@ def create_schedule():
 
     Request body:
         name: Schedule name (required)
-        config_file: Path to YAML config (required)
+        config_id: Database config ID (required)
         cron_expression: Cron expression (required, e.g., '0 2 * * *')
         enabled: Whether schedule is active (optional, default: true)
 
@@ -99,7 +99,7 @@ def create_schedule():
         data = request.get_json() or {}
 
         # Validate required fields
-        required = ['name', 'config_file', 'cron_expression']
+        required = ['name', 'config_id', 'cron_expression']
         missing = [field for field in required if field not in data]
         if missing:
             return jsonify({'error': f'Missing required fields: {", ".join(missing)}'}), 400
@@ -108,7 +108,7 @@ def create_schedule():
         schedule_service = ScheduleService(current_app.db_session)
         schedule_id = schedule_service.create_schedule(
             name=data['name'],
-            config_file=data['config_file'],
+            config_id=data['config_id'],
             cron_expression=data['cron_expression'],
             enabled=data.get('enabled', True)
         )
@@ -121,7 +121,7 @@ def create_schedule():
             try:
                 current_app.scheduler.add_scheduled_scan(
                     schedule_id=schedule_id,
-                    config_file=schedule['config_file'],
+                    config_id=schedule['config_id'],
                     cron_expression=schedule['cron_expression']
                 )
                 logger.info(f"Schedule {schedule_id} added to APScheduler")
@@ -154,7 +154,7 @@ def update_schedule(schedule_id):
 
     Request body:
         name: Schedule name (optional)
-        config_file: Path to YAML config (optional)
+        config_id: Database config ID (optional)
         cron_expression: Cron expression (optional)
         enabled: Whether schedule is active (optional)
 
@@ -181,7 +181,7 @@ def update_schedule(schedule_id):
             try:
                 # If cron expression or config changed, or enabled status changed
                 cron_changed = 'cron_expression' in data
-                config_changed = 'config_file' in data
+                config_changed = 'config_id' in data
                 enabled_changed = 'enabled' in data
 
                 if enabled_changed:
@@ -189,7 +189,7 @@ def update_schedule(schedule_id):
                         # Re-add to scheduler (replaces existing)
                         current_app.scheduler.add_scheduled_scan(
                             schedule_id=schedule_id,
-                            config_file=updated_schedule['config_file'],
+                            config_id=updated_schedule['config_id'],
                             cron_expression=updated_schedule['cron_expression']
                         )
                         logger.info(f"Schedule {schedule_id} enabled and added to APScheduler")
@@ -201,7 +201,7 @@ def update_schedule(schedule_id):
                     # Reload schedule in APScheduler
                     current_app.scheduler.add_scheduled_scan(
                         schedule_id=schedule_id,
-                        config_file=updated_schedule['config_file'],
+                        config_id=updated_schedule['config_id'],
                         cron_expression=updated_schedule['cron_expression']
                     )
                     logger.info(f"Schedule {schedule_id} reloaded in APScheduler")
@@ -293,7 +293,7 @@ def trigger_schedule(schedule_id):
         scheduler = current_app.scheduler if hasattr(current_app, 'scheduler') else None
 
         scan_id = scan_service.trigger_scan(
-            config_file=schedule['config_file'],
+            config_id=schedule['config_id'],
             triggered_by='manual',
             schedule_id=schedule_id,
             scheduler=scheduler

app/web/api/settings.py

@@ -75,6 +75,12 @@ def update_settings():
             'status': 'success',
             'message': f'Updated {len(settings_dict)} settings'
         })
+    except ValueError as e:
+        # Handle read-only setting attempts
+        return jsonify({
+            'status': 'error',
+            'message': str(e)
+        }), 403
     except Exception as e:
         current_app.logger.error(f"Failed to update settings: {e}")
         return jsonify({
@@ -112,7 +118,8 @@ def get_setting(key):
         return jsonify({
             'status': 'success',
             'key': key,
-            'value': value
+            'value': value,
+            'read_only': settings_manager._is_read_only(key)
         })
     except Exception as e:
         current_app.logger.error(f"Failed to retrieve setting {key}: {e}")
@@ -154,6 +161,12 @@ def update_setting(key):
             'status': 'success',
             'message': f'Setting "{key}" updated'
         })
+    except ValueError as e:
+        # Handle read-only setting attempts
+        return jsonify({
+            'status': 'error',
+            'message': str(e)
+        }), 403
     except Exception as e:
         current_app.logger.error(f"Failed to update setting {key}: {e}")
         return jsonify({
@@ -176,6 +189,14 @@ def delete_setting(key):
     """
     try:
         settings_manager = get_settings_manager()
+
+        # Prevent deletion of read-only settings
+        if settings_manager._is_read_only(key):
+            return jsonify({
+                'status': 'error',
+                'message': f'Setting "{key}" is read-only and cannot be deleted'
+            }), 403
+
         deleted = settings_manager.delete(key)
 
         if not deleted:

app/web/api/sites.py

@@ -0,0 +1,661 @@
+"""
+Sites API blueprint.
+
+Handles endpoints for managing reusable site definitions, including CIDR ranges
+and IP-level overrides.
+"""
+
+import logging
+from flask import Blueprint, current_app, jsonify, request
+from sqlalchemy.exc import SQLAlchemyError
+
+from web.auth.decorators import api_auth_required
+from web.services.site_service import SiteService
+from web.utils.pagination import validate_page_params
+
+bp = Blueprint('sites', __name__)
+logger = logging.getLogger(__name__)
+
+
+@bp.route('', methods=['GET'])
+@api_auth_required
+def list_sites():
+    """
+    List all sites with pagination.
+
+    Query params:
+        page: Page number (default: 1)
+        per_page: Items per page (default: 20, max: 100)
+        all: If 'true', returns all sites without pagination (for dropdowns)
+
+    Returns:
+        JSON response with sites list and pagination info
+    """
+    try:
+        # Check if requesting all sites (no pagination)
+        if request.args.get('all', '').lower() == 'true':
+            site_service = SiteService(current_app.db_session)
+            sites = site_service.list_all_sites()
+            ip_stats = site_service.get_global_ip_stats()
+
+            logger.info(f"Listed all sites (count={len(sites)})")
+            return jsonify({
+                'sites': sites,
+                'total_ips': ip_stats['total_ips'],
+                'unique_ips': ip_stats['unique_ips'],
+                'duplicate_ips': ip_stats['duplicate_ips']
+            })
+
+        # Get and validate query parameters
+        page = request.args.get('page', 1, type=int)
+        per_page = request.args.get('per_page', 20, type=int)
+
+        # Validate pagination params
+        page, per_page = validate_page_params(page, per_page)
+
+        # Get sites from service
+        site_service = SiteService(current_app.db_session)
+        paginated_result = site_service.list_sites(page=page, per_page=per_page)
+
+        logger.info(f"Listed sites: page={page}, per_page={per_page}, total={paginated_result.total}")
+
+        return jsonify({
+            'sites': paginated_result.items,
+            'total': paginated_result.total,
+            'page': paginated_result.page,
+            'per_page': paginated_result.per_page,
+            'total_pages': paginated_result.pages,
+            'has_prev': paginated_result.has_prev,
+            'has_next': paginated_result.has_next
+        })
+
+    except ValueError as e:
+        logger.warning(f"Invalid request parameters: {str(e)}")
+        return jsonify({
+            'error': 'Invalid request',
+            'message': str(e)
+        }), 400
+    except SQLAlchemyError as e:
+        logger.error(f"Database error listing sites: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to retrieve sites'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error listing sites: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:site_id>', methods=['GET'])
+@api_auth_required
+def get_site(site_id):
+    """
+    Get details for a specific site.
+
+    Args:
+        site_id: Site ID
+
+    Returns:
+        JSON response with site details including CIDRs and IP overrides
+    """
+    try:
+        site_service = SiteService(current_app.db_session)
+        site = site_service.get_site(site_id)
+
+        if not site:
+            logger.warning(f"Site not found: {site_id}")
+            return jsonify({
+                'error': 'Not found',
+                'message': f'Site with ID {site_id} not found'
+            }), 404
+
+        logger.info(f"Retrieved site details: {site_id}")
+        return jsonify(site)
+
+    except SQLAlchemyError as e:
+        logger.error(f"Database error retrieving site {site_id}: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to retrieve site'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error retrieving site {site_id}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('', methods=['POST'])
+@api_auth_required
+def create_site():
+    """
+    Create a new site.
+
+    Request body:
+        name: Site name (required, must be unique)
+        description: Site description (optional)
+        cidrs: List of CIDR definitions (optional, but recommended)
+            [
+                {
+                    "cidr": "10.0.0.0/24",
+                    "expected_ping": true,
+                    "expected_tcp_ports": [22, 80, 443],
+                    "expected_udp_ports": [53]
+                }
+            ]
+
+    Returns:
+        JSON response with created site data
+    """
+    try:
+        data = request.get_json() or {}
+
+        # Validate required fields
+        name = data.get('name')
+        if not name:
+            logger.warning("Site creation request missing name")
+            return jsonify({
+                'error': 'Invalid request',
+                'message': 'name is required'
+            }), 400
+
+        description = data.get('description')
+
+        # Create site (empty initially)
+        site_service = SiteService(current_app.db_session)
+        site = site_service.create_site(
+            name=name,
+            description=description
+        )
+
+        logger.info(f"Created site '{name}' (id={site['id']})")
+        return jsonify(site), 201
+
+    except ValueError as e:
+        logger.warning(f"Invalid site creation request: {str(e)}")
+        return jsonify({
+            'error': 'Invalid request',
+            'message': str(e)
+        }), 400
+    except SQLAlchemyError as e:
+        logger.error(f"Database error creating site: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to create site'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error creating site: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:site_id>', methods=['PUT'])
+@api_auth_required
+def update_site(site_id):
+    """
+    Update site metadata (name and/or description).
+
+    Args:
+        site_id: Site ID
+
+    Request body:
+        name: New site name (optional, must be unique)
+        description: New description (optional)
+
+    Returns:
+        JSON response with updated site data
+    """
+    try:
+        data = request.get_json() or {}
+
+        name = data.get('name')
+        description = data.get('description')
+
+        # Update site
+        site_service = SiteService(current_app.db_session)
+        site = site_service.update_site(
+            site_id=site_id,
+            name=name,
+            description=description
+        )
+
+        logger.info(f"Updated site {site_id}")
+        return jsonify(site)
+
+    except ValueError as e:
+        logger.warning(f"Invalid site update request: {str(e)}")
+        return jsonify({
+            'error': 'Invalid request',
+            'message': str(e)
+        }), 400
+    except SQLAlchemyError as e:
+        logger.error(f"Database error updating site {site_id}: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to update site'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error updating site {site_id}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:site_id>', methods=['DELETE'])
+@api_auth_required
+def delete_site(site_id):
+    """
+    Delete a site.
+
+    Prevents deletion if site is used in any scan.
+
+    Args:
+        site_id: Site ID
+
+    Returns:
+        JSON response with success message
+    """
+    try:
+        site_service = SiteService(current_app.db_session)
+        site_service.delete_site(site_id)
+
+        logger.info(f"Deleted site {site_id}")
+        return jsonify({
+            'message': f'Site {site_id} deleted successfully'
+        })
+
+    except ValueError as e:
+        logger.warning(f"Cannot delete site {site_id}: {str(e)}")
+        return jsonify({
+            'error': 'Invalid request',
+            'message': str(e)
+        }), 400
+    except SQLAlchemyError as e:
+        logger.error(f"Database error deleting site {site_id}: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to delete site'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error deleting site {site_id}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:site_id>/ips/bulk', methods=['POST'])
+@api_auth_required
+def bulk_add_ips(site_id):
+    """
+    Bulk add IPs to a site from CIDR or list.
+
+    Args:
+        site_id: Site ID
+
+    Request body:
+        source_type: "cidr" or "list" (required)
+        cidr: CIDR notation if source_type="cidr" (e.g., "10.0.0.0/24")
+        ips: List of IP addresses if source_type="list" (e.g., ["10.0.0.1", "10.0.0.2"])
+        expected_ping: Expected ping response for all IPs (optional)
+        expected_tcp_ports: List of expected TCP ports for all IPs (optional)
+        expected_udp_ports: List of expected UDP ports for all IPs (optional)
+
+    Returns:
+        JSON response with count of IPs added and any errors
+    """
+    try:
+        data = request.get_json() or {}
+
+        source_type = data.get('source_type')
+        if source_type not in ['cidr', 'list']:
+            return jsonify({
+                'error': 'Invalid request',
+                'message': 'source_type must be "cidr" or "list"'
+            }), 400
+
+        expected_ping = data.get('expected_ping')
+        expected_tcp_ports = data.get('expected_tcp_ports', [])
+        expected_udp_ports = data.get('expected_udp_ports', [])
+
+        site_service = SiteService(current_app.db_session)
+
+        if source_type == 'cidr':
+            cidr = data.get('cidr')
+            if not cidr:
+                return jsonify({
+                    'error': 'Invalid request',
+                    'message': 'cidr is required when source_type="cidr"'
+                }), 400
+
+            result = site_service.bulk_add_ips_from_cidr(
+                site_id=site_id,
+                cidr=cidr,
+                expected_ping=expected_ping,
+                expected_tcp_ports=expected_tcp_ports,
+                expected_udp_ports=expected_udp_ports
+            )
+
+            logger.info(f"Bulk added {result['ip_count']} IPs from CIDR '{cidr}' to site {site_id}")
+            return jsonify(result), 201
+
+        else:  # source_type == 'list'
+            ip_list = data.get('ips', [])
+            if not isinstance(ip_list, list):
+                return jsonify({
+                    'error': 'Invalid request',
+                    'message': 'ips must be a list when source_type="list"'
+                }), 400
+
+            result = site_service.bulk_add_ips_from_list(
+                site_id=site_id,
+                ip_list=ip_list,
+                expected_ping=expected_ping,
+                expected_tcp_ports=expected_tcp_ports,
+                expected_udp_ports=expected_udp_ports
+            )
+
+            logger.info(f"Bulk added {result['ip_count']} IPs from list to site {site_id}")
+            return jsonify(result), 201
+
+    except ValueError as e:
+        logger.warning(f"Invalid bulk IP request: {str(e)}")
+        return jsonify({
+            'error': 'Invalid request',
+            'message': str(e)
+        }), 400
+    except SQLAlchemyError as e:
+        logger.error(f"Database error bulk adding IPs to site {site_id}: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to add IPs'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error bulk adding IPs to site {site_id}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:site_id>/ips', methods=['GET'])
+@api_auth_required
+def list_ips(site_id):
+    """
+    List IPs in a site with pagination.
+
+    Query params:
+        page: Page number (default: 1)
+        per_page: Items per page (default: 50, max: 200)
+
+    Returns:
+        JSON response with IPs list and pagination info
+    """
+    try:
+        # Get and validate query parameters
+        page = request.args.get('page', 1, type=int)
+        per_page = request.args.get('per_page', 50, type=int)
+
+        # Validate pagination params
+        page, per_page = validate_page_params(page, per_page, max_per_page=200)
+
+        # Get IPs from service
+        site_service = SiteService(current_app.db_session)
+        paginated_result = site_service.list_ips(
+            site_id=site_id,
+            page=page,
+            per_page=per_page
+        )
+
+        logger.info(f"Listed IPs for site {site_id}: page={page}, per_page={per_page}, total={paginated_result.total}")
+
+        return jsonify({
+            'ips': paginated_result.items,
+            'total': paginated_result.total,
+            'page': paginated_result.page,
+            'per_page': paginated_result.per_page,
+            'total_pages': paginated_result.pages,
+            'has_prev': paginated_result.has_prev,
+            'has_next': paginated_result.has_next
+        })
+
+    except ValueError as e:
+        logger.warning(f"Invalid request parameters: {str(e)}")
+        return jsonify({
+            'error': 'Invalid request',
+            'message': str(e)
+        }), 400
+    except SQLAlchemyError as e:
+        logger.error(f"Database error listing IPs for site {site_id}: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to retrieve IPs'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error listing IPs for site {site_id}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:site_id>/ips', methods=['POST'])
+@api_auth_required
+def add_standalone_ip(site_id):
+    """
+    Add a standalone IP (without CIDR parent) to a site.
+
+    Args:
+        site_id: Site ID
+
+    Request body:
+        ip_address: IP address (required)
+        expected_ping: Expected ping response (optional)
+        expected_tcp_ports: List of expected TCP ports (optional)
+        expected_udp_ports: List of expected UDP ports (optional)
+
+    Returns:
+        JSON response with created IP data
+    """
+    try:
+        data = request.get_json() or {}
+
+        # Validate required fields
+        ip_address = data.get('ip_address')
+        if not ip_address:
+            logger.warning("Standalone IP creation request missing ip_address")
+            return jsonify({
+                'error': 'Invalid request',
+                'message': 'ip_address is required'
+            }), 400
+
+        expected_ping = data.get('expected_ping')
+        expected_tcp_ports = data.get('expected_tcp_ports', [])
+        expected_udp_ports = data.get('expected_udp_ports', [])
+
+        # Add standalone IP
+        site_service = SiteService(current_app.db_session)
+        ip_data = site_service.add_standalone_ip(
+            site_id=site_id,
+            ip_address=ip_address,
+            expected_ping=expected_ping,
+            expected_tcp_ports=expected_tcp_ports,
+            expected_udp_ports=expected_udp_ports
+        )
+
+        logger.info(f"Added standalone IP '{ip_address}' to site {site_id}")
+        return jsonify(ip_data), 201
+
+    except ValueError as e:
+        logger.warning(f"Invalid standalone IP creation request: {str(e)}")
+        return jsonify({
+            'error': 'Invalid request',
+            'message': str(e)
+        }), 400
+    except SQLAlchemyError as e:
+        logger.error(f"Database error adding standalone IP to site {site_id}: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to add IP'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error adding standalone IP to site {site_id}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:site_id>/ips/<int:ip_id>', methods=['PUT'])
+@api_auth_required
+def update_ip_settings(site_id, ip_id):
+    """
+    Update settings for an individual IP.
+
+    Args:
+        site_id: Site ID
+        ip_id: IP ID
+
+    Request body:
+        expected_ping: New ping expectation (optional)
+        expected_tcp_ports: New TCP ports expectation (optional)
+        expected_udp_ports: New UDP ports expectation (optional)
+
+    Returns:
+        JSON response with updated IP data
+    """
+    try:
+        data = request.get_json() or {}
+
+        expected_ping = data.get('expected_ping')
+        expected_tcp_ports = data.get('expected_tcp_ports')
+        expected_udp_ports = data.get('expected_udp_ports')
+
+        # Update IP settings
+        site_service = SiteService(current_app.db_session)
+        ip_data = site_service.update_ip_settings(
+            site_id=site_id,
+            ip_id=ip_id,
+            expected_ping=expected_ping,
+            expected_tcp_ports=expected_tcp_ports,
+            expected_udp_ports=expected_udp_ports
+        )
+
+        logger.info(f"Updated IP {ip_id} in site {site_id}")
+        return jsonify(ip_data)
+
+    except ValueError as e:
+        logger.warning(f"Invalid IP update request: {str(e)}")
+        return jsonify({
+            'error': 'Invalid request',
+            'message': str(e)
+        }), 400
+    except SQLAlchemyError as e:
+        logger.error(f"Database error updating IP {ip_id} in site {site_id}: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to update IP'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error updating IP {ip_id} in site {site_id}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:site_id>/ips/<int:ip_id>', methods=['DELETE'])
+@api_auth_required
+def remove_ip(site_id, ip_id):
+    """
+    Remove an IP from a site.
+
+    Args:
+        site_id: Site ID
+        ip_id: IP ID
+
+    Returns:
+        JSON response with success message
+    """
+    try:
+        site_service = SiteService(current_app.db_session)
+        site_service.remove_ip(site_id, ip_id)
+
+        logger.info(f"Removed IP {ip_id} from site {site_id}")
+        return jsonify({
+            'message': f'IP {ip_id} removed successfully'
+        })
+
+    except ValueError as e:
+        logger.warning(f"Cannot remove IP {ip_id}: {str(e)}")
+        return jsonify({
+            'error': 'Invalid request',
+            'message': str(e)
+        }), 400
+    except SQLAlchemyError as e:
+        logger.error(f"Database error removing IP {ip_id}: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to remove IP'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error removing IP {ip_id}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500
+
+
+@bp.route('/<int:site_id>/usage', methods=['GET'])
+@api_auth_required
+def get_site_usage(site_id):
+    """
+    Get list of scans that use this site.
+
+    Args:
+        site_id: Site ID
+
+    Returns:
+        JSON response with list of scans
+    """
+    try:
+        site_service = SiteService(current_app.db_session)
+
+        # First check if site exists
+        site = site_service.get_site(site_id)
+        if not site:
+            logger.warning(f"Site not found: {site_id}")
+            return jsonify({
+                'error': 'Not found',
+                'message': f'Site with ID {site_id} not found'
+            }), 404
+
+        scans = site_service.get_scan_usage(site_id)
+
+        logger.info(f"Retrieved usage for site {site_id} (count={len(scans)})")
+        return jsonify({
+            'site_id': site_id,
+            'site_name': site['name'],
+            'scans': scans,
+            'count': len(scans)
+        })
+
+    except SQLAlchemyError as e:
+        logger.error(f"Database error retrieving site usage {site_id}: {str(e)}")
+        return jsonify({
+            'error': 'Database error',
+            'message': 'Failed to retrieve site usage'
+        }), 500
+    except Exception as e:
+        logger.error(f"Unexpected error retrieving site usage {site_id}: {str(e)}", exc_info=True)
+        return jsonify({
+            'error': 'Internal server error',
+            'message': 'An unexpected error occurred'
+        }), 500

app/web/api/stats.py

@@ -198,12 +198,12 @@ def scan_history(scan_id):
         if not reference_scan:
             return jsonify({'error': 'Scan not found'}), 404
 
-        config_file = reference_scan.config_file
+        config_id = reference_scan.config_id
 
-        # Query historical scans with the same config file
+        # Query historical scans with the same config_id
         historical_scans = (
             db_session.query(Scan)
-            .filter(Scan.config_file == config_file)
+            .filter(Scan.config_id == config_id)
             .filter(Scan.status == 'completed')
             .order_by(Scan.timestamp.desc())
             .limit(limit)
@@ -247,7 +247,7 @@ def scan_history(scan_id):
             'scans': scans_data,
             'labels': labels,
             'port_counts': port_counts,
-            'config_file': config_file
+            'config_id': config_id
         }), 200
 
     except SQLAlchemyError as e:

app/web/api/webhooks.py

@@ -0,0 +1,677 @@
+"""
+Webhooks API blueprint.
+
+Handles endpoints for managing webhook configurations and viewing delivery logs.
+"""
+
+import json
+from datetime import datetime, timezone
+from flask import Blueprint, jsonify, request, current_app
+
+from web.auth.decorators import api_auth_required
+from web.models import Webhook, WebhookDeliveryLog, Alert
+from web.services.webhook_service import WebhookService
+from web.services.template_service import get_template_service
+
+bp = Blueprint('webhooks_api', __name__)
+
+
+@bp.route('', methods=['GET'])
+@api_auth_required
+def list_webhooks():
+    """
+    List all webhooks with optional filtering.
+
+    Query params:
+        page: Page number (default: 1)
+        per_page: Items per page (default: 20)
+        enabled: Filter by enabled status (true/false)
+
+    Returns:
+        JSON response with webhooks list
+    """
+    # Get query parameters
+    page = request.args.get('page', 1, type=int)
+    per_page = min(request.args.get('per_page', 20, type=int), 100)  # Max 100 items
+    enabled = request.args.get('enabled')
+
+    # Build query
+    query = current_app.db_session.query(Webhook)
+
+    # Apply enabled filter
+    if enabled is not None:
+        enabled_bool = enabled.lower() == 'true'
+        query = query.filter(Webhook.enabled == enabled_bool)
+
+    # Order by name
+    query = query.order_by(Webhook.name)
+
+    # Paginate
+    total = query.count()
+    webhooks = query.offset((page - 1) * per_page).limit(per_page).all()
+
+    # Format response
+    webhooks_data = []
+
+    for webhook in webhooks:
+        # Parse JSON fields
+        alert_types = json.loads(webhook.alert_types) if webhook.alert_types else None
+        severity_filter = json.loads(webhook.severity_filter) if webhook.severity_filter else None
+        custom_headers = json.loads(webhook.custom_headers) if webhook.custom_headers else None
+
+        webhooks_data.append({
+            'id': webhook.id,
+            'name': webhook.name,
+            'url': webhook.url,
+            'enabled': webhook.enabled,
+            'auth_type': webhook.auth_type,
+            'auth_token': '***ENCRYPTED***' if webhook.auth_token else None,  # Mask sensitive data
+            'custom_headers': custom_headers,
+            'alert_types': alert_types,
+            'severity_filter': severity_filter,
+            'timeout': webhook.timeout,
+            'retry_count': webhook.retry_count,
+            'created_at': webhook.created_at.isoformat() if webhook.created_at else None,
+            'updated_at': webhook.updated_at.isoformat() if webhook.updated_at else None
+        })
+
+    return jsonify({
+        'webhooks': webhooks_data,
+        'total': total,
+        'page': page,
+        'per_page': per_page,
+        'pages': (total + per_page - 1) // per_page
+    })
+
+
+@bp.route('/<int:webhook_id>', methods=['GET'])
+@api_auth_required
+def get_webhook(webhook_id):
+    """
+    Get a specific webhook by ID.
+
+    Args:
+        webhook_id: Webhook ID
+
+    Returns:
+        JSON response with webhook details
+    """
+    webhook = current_app.db_session.query(Webhook).filter(Webhook.id == webhook_id).first()
+
+    if not webhook:
+        return jsonify({
+            'status': 'error',
+            'message': f'Webhook {webhook_id} not found'
+        }), 404
+
+    # Parse JSON fields
+    alert_types = json.loads(webhook.alert_types) if webhook.alert_types else None
+    severity_filter = json.loads(webhook.severity_filter) if webhook.severity_filter else None
+    custom_headers = json.loads(webhook.custom_headers) if webhook.custom_headers else None
+
+    return jsonify({
+        'webhook': {
+            'id': webhook.id,
+            'name': webhook.name,
+            'url': webhook.url,
+            'enabled': webhook.enabled,
+            'auth_type': webhook.auth_type,
+            'auth_token': '***ENCRYPTED***' if webhook.auth_token else None,
+            'custom_headers': custom_headers,
+            'alert_types': alert_types,
+            'severity_filter': severity_filter,
+            'timeout': webhook.timeout,
+            'retry_count': webhook.retry_count,
+            'created_at': webhook.created_at.isoformat() if webhook.created_at else None,
+            'updated_at': webhook.updated_at.isoformat() if webhook.updated_at else None
+        }
+    })
+
+
+@bp.route('', methods=['POST'])
+@api_auth_required
+def create_webhook():
+    """
+    Create a new webhook.
+
+    Request body:
+        name: Webhook name (required)
+        url: Webhook URL (required)
+        enabled: Whether webhook is enabled (default: true)
+        auth_type: Authentication type (none, bearer, basic, custom)
+        auth_token: Authentication token (encrypted on storage)
+        custom_headers: JSON object with custom headers
+        alert_types: Array of alert types to filter
+        severity_filter: Array of severities to filter
+        timeout: Request timeout in seconds (default: 10)
+        retry_count: Number of retry attempts (default: 3)
+        template: Jinja2 template for custom payload (optional)
+        template_format: Template format - 'json' or 'text' (default: json)
+        content_type_override: Custom Content-Type header (optional)
+
+    Returns:
+        JSON response with created webhook
+    """
+    data = request.get_json() or {}
+
+    # Validate required fields
+    if not data.get('name'):
+        return jsonify({
+            'status': 'error',
+            'message': 'name is required'
+        }), 400
+
+    if not data.get('url'):
+        return jsonify({
+            'status': 'error',
+            'message': 'url is required'
+        }), 400
+
+    # Validate auth_type
+    valid_auth_types = ['none', 'bearer', 'basic', 'custom']
+    auth_type = data.get('auth_type', 'none')
+    if auth_type not in valid_auth_types:
+        return jsonify({
+            'status': 'error',
+            'message': f'Invalid auth_type. Must be one of: {", ".join(valid_auth_types)}'
+        }), 400
+
+    # Validate template_format
+    valid_template_formats = ['json', 'text']
+    template_format = data.get('template_format', 'json')
+    if template_format not in valid_template_formats:
+        return jsonify({
+            'status': 'error',
+            'message': f'Invalid template_format. Must be one of: {", ".join(valid_template_formats)}'
+        }), 400
+
+    # Validate template if provided
+    template = data.get('template')
+    if template:
+        template_service = get_template_service()
+        is_valid, error_msg = template_service.validate_template(template, template_format)
+        if not is_valid:
+            return jsonify({
+                'status': 'error',
+                'message': f'Invalid template: {error_msg}'
+            }), 400
+
+    try:
+        webhook_service = WebhookService(current_app.db_session)
+
+        # Encrypt auth_token if provided
+        auth_token = None
+        if data.get('auth_token'):
+            auth_token = webhook_service._encrypt_value(data['auth_token'])
+
+        # Serialize JSON fields
+        alert_types = json.dumps(data['alert_types']) if data.get('alert_types') else None
+        severity_filter = json.dumps(data['severity_filter']) if data.get('severity_filter') else None
+        custom_headers = json.dumps(data['custom_headers']) if data.get('custom_headers') else None
+
+        # Create webhook
+        webhook = Webhook(
+            name=data['name'],
+            url=data['url'],
+            enabled=data.get('enabled', True),
+            auth_type=auth_type,
+            auth_token=auth_token,
+            custom_headers=custom_headers,
+            alert_types=alert_types,
+            severity_filter=severity_filter,
+            timeout=data.get('timeout', 10),
+            retry_count=data.get('retry_count', 3),
+            template=template,
+            template_format=template_format,
+            content_type_override=data.get('content_type_override'),
+            created_at=datetime.now(timezone.utc),
+            updated_at=datetime.now(timezone.utc)
+        )
+
+        current_app.db_session.add(webhook)
+        current_app.db_session.commit()
+
+        # Parse for response
+        alert_types_parsed = json.loads(alert_types) if alert_types else None
+        severity_filter_parsed = json.loads(severity_filter) if severity_filter else None
+        custom_headers_parsed = json.loads(custom_headers) if custom_headers else None
+
+        return jsonify({
+            'status': 'success',
+            'message': 'Webhook created successfully',
+            'webhook': {
+                'id': webhook.id,
+                'name': webhook.name,
+                'url': webhook.url,
+                'enabled': webhook.enabled,
+                'auth_type': webhook.auth_type,
+                'alert_types': alert_types_parsed,
+                'severity_filter': severity_filter_parsed,
+                'custom_headers': custom_headers_parsed,
+                'timeout': webhook.timeout,
+                'retry_count': webhook.retry_count,
+                'template': webhook.template,
+                'template_format': webhook.template_format,
+                'content_type_override': webhook.content_type_override,
+                'created_at': webhook.created_at.isoformat()
+            }
+        }), 201
+
+    except Exception as e:
+        current_app.db_session.rollback()
+        return jsonify({
+            'status': 'error',
+            'message': f'Failed to create webhook: {str(e)}'
+        }), 500
+
+
+@bp.route('/<int:webhook_id>', methods=['PUT'])
+@api_auth_required
+def update_webhook(webhook_id):
+    """
+    Update an existing webhook.
+
+    Args:
+        webhook_id: Webhook ID
+
+    Request body (all optional):
+        name: Webhook name
+        url: Webhook URL
+        enabled: Whether webhook is enabled
+        auth_type: Authentication type
+        auth_token: Authentication token
+        custom_headers: JSON object with custom headers
+        alert_types: Array of alert types
+        severity_filter: Array of severities
+        timeout: Request timeout
+        retry_count: Retry attempts
+        template: Jinja2 template for custom payload
+        template_format: Template format - 'json' or 'text'
+        content_type_override: Custom Content-Type header
+
+    Returns:
+        JSON response with update status
+    """
+    webhook = current_app.db_session.query(Webhook).filter(Webhook.id == webhook_id).first()
+
+    if not webhook:
+        return jsonify({
+            'status': 'error',
+            'message': f'Webhook {webhook_id} not found'
+        }), 404
+
+    data = request.get_json() or {}
+
+    # Validate auth_type if provided
+    if 'auth_type' in data:
+        valid_auth_types = ['none', 'bearer', 'basic', 'custom']
+        if data['auth_type'] not in valid_auth_types:
+            return jsonify({
+                'status': 'error',
+                'message': f'Invalid auth_type. Must be one of: {", ".join(valid_auth_types)}'
+            }), 400
+
+    # Validate template_format if provided
+    if 'template_format' in data:
+        valid_template_formats = ['json', 'text']
+        if data['template_format'] not in valid_template_formats:
+            return jsonify({
+                'status': 'error',
+                'message': f'Invalid template_format. Must be one of: {", ".join(valid_template_formats)}'
+            }), 400
+
+    # Validate template if provided
+    if 'template' in data and data['template']:
+        template_format = data.get('template_format', webhook.template_format or 'json')
+        template_service = get_template_service()
+        is_valid, error_msg = template_service.validate_template(data['template'], template_format)
+        if not is_valid:
+            return jsonify({
+                'status': 'error',
+                'message': f'Invalid template: {error_msg}'
+            }), 400
+
+    try:
+        webhook_service = WebhookService(current_app.db_session)
+
+        # Update fields if provided
+        if 'name' in data:
+            webhook.name = data['name']
+        if 'url' in data:
+            webhook.url = data['url']
+        if 'enabled' in data:
+            webhook.enabled = data['enabled']
+        if 'auth_type' in data:
+            webhook.auth_type = data['auth_type']
+        if 'auth_token' in data:
+            # Encrypt new token
+            webhook.auth_token = webhook_service._encrypt_value(data['auth_token'])
+        if 'custom_headers' in data:
+            webhook.custom_headers = json.dumps(data['custom_headers']) if data['custom_headers'] else None
+        if 'alert_types' in data:
+            webhook.alert_types = json.dumps(data['alert_types']) if data['alert_types'] else None
+        if 'severity_filter' in data:
+            webhook.severity_filter = json.dumps(data['severity_filter']) if data['severity_filter'] else None
+        if 'timeout' in data:
+            webhook.timeout = data['timeout']
+        if 'retry_count' in data:
+            webhook.retry_count = data['retry_count']
+        if 'template' in data:
+            webhook.template = data['template']
+        if 'template_format' in data:
+            webhook.template_format = data['template_format']
+        if 'content_type_override' in data:
+            webhook.content_type_override = data['content_type_override']
+
+        webhook.updated_at = datetime.now(timezone.utc)
+        current_app.db_session.commit()
+
+        # Parse for response
+        alert_types = json.loads(webhook.alert_types) if webhook.alert_types else None
+        severity_filter = json.loads(webhook.severity_filter) if webhook.severity_filter else None
+        custom_headers = json.loads(webhook.custom_headers) if webhook.custom_headers else None
+
+        return jsonify({
+            'status': 'success',
+            'message': 'Webhook updated successfully',
+            'webhook': {
+                'id': webhook.id,
+                'name': webhook.name,
+                'url': webhook.url,
+                'enabled': webhook.enabled,
+                'auth_type': webhook.auth_type,
+                'alert_types': alert_types,
+                'severity_filter': severity_filter,
+                'custom_headers': custom_headers,
+                'timeout': webhook.timeout,
+                'retry_count': webhook.retry_count,
+                'template': webhook.template,
+                'template_format': webhook.template_format,
+                'content_type_override': webhook.content_type_override,
+                'updated_at': webhook.updated_at.isoformat()
+            }
+        })
+
+    except Exception as e:
+        current_app.db_session.rollback()
+        return jsonify({
+            'status': 'error',
+            'message': f'Failed to update webhook: {str(e)}'
+        }), 500
+
+
+@bp.route('/<int:webhook_id>', methods=['DELETE'])
+@api_auth_required
+def delete_webhook(webhook_id):
+    """
+    Delete a webhook.
+
+    Args:
+        webhook_id: Webhook ID
+
+    Returns:
+        JSON response with deletion status
+    """
+    webhook = current_app.db_session.query(Webhook).filter(Webhook.id == webhook_id).first()
+
+    if not webhook:
+        return jsonify({
+            'status': 'error',
+            'message': f'Webhook {webhook_id} not found'
+        }), 404
+
+    try:
+        # Delete webhook (delivery logs will be cascade deleted)
+        current_app.db_session.delete(webhook)
+        current_app.db_session.commit()
+
+        return jsonify({
+            'status': 'success',
+            'message': f'Webhook {webhook_id} deleted successfully'
+        })
+
+    except Exception as e:
+        current_app.db_session.rollback()
+        return jsonify({
+            'status': 'error',
+            'message': f'Failed to delete webhook: {str(e)}'
+        }), 500
+
+
+@bp.route('/<int:webhook_id>/test', methods=['POST'])
+@api_auth_required
+def test_webhook(webhook_id):
+    """
+    Send a test payload to a webhook.
+
+    Args:
+        webhook_id: Webhook ID
+
+    Returns:
+        JSON response with test result
+    """
+    webhook = current_app.db_session.query(Webhook).filter(Webhook.id == webhook_id).first()
+
+    if not webhook:
+        return jsonify({
+            'status': 'error',
+            'message': f'Webhook {webhook_id} not found'
+        }), 404
+
+    # Test webhook delivery
+    webhook_service = WebhookService(current_app.db_session)
+    result = webhook_service.test_webhook(webhook_id)
+
+    return jsonify({
+        'status': 'success' if result['success'] else 'error',
+        'message': result['message'],
+        'status_code': result['status_code'],
+        'response_body': result.get('response_body')
+    })
+
+
+@bp.route('/<int:webhook_id>/logs', methods=['GET'])
+@api_auth_required
+def get_webhook_logs(webhook_id):
+    """
+    Get delivery logs for a specific webhook.
+
+    Args:
+        webhook_id: Webhook ID
+
+    Query params:
+        page: Page number (default: 1)
+        per_page: Items per page (default: 20)
+        status: Filter by status (success/failed)
+
+    Returns:
+        JSON response with delivery logs
+    """
+    webhook = current_app.db_session.query(Webhook).filter(Webhook.id == webhook_id).first()
+
+    if not webhook:
+        return jsonify({
+            'status': 'error',
+            'message': f'Webhook {webhook_id} not found'
+        }), 404
+
+    # Get query parameters
+    page = request.args.get('page', 1, type=int)
+    per_page = min(request.args.get('per_page', 20, type=int), 100)
+    status_filter = request.args.get('status')
+
+    # Build query
+    query = current_app.db_session.query(WebhookDeliveryLog).filter(
+        WebhookDeliveryLog.webhook_id == webhook_id
+    )
+
+    # Apply status filter
+    if status_filter:
+        query = query.filter(WebhookDeliveryLog.status == status_filter)
+
+    # Order by most recent first
+    query = query.order_by(WebhookDeliveryLog.delivered_at.desc())
+
+    # Paginate
+    total = query.count()
+    logs = query.offset((page - 1) * per_page).limit(per_page).all()
+
+    # Format response
+    logs_data = []
+    for log in logs:
+        # Get alert info
+        alert = current_app.db_session.query(Alert).filter(Alert.id == log.alert_id).first()
+
+        logs_data.append({
+            'id': log.id,
+            'alert_id': log.alert_id,
+            'alert_type': alert.alert_type if alert else None,
+            'alert_message': alert.message if alert else None,
+            'status': log.status,
+            'response_code': log.response_code,
+            'response_body': log.response_body,
+            'error_message': log.error_message,
+            'attempt_number': log.attempt_number,
+            'delivered_at': log.delivered_at.isoformat() if log.delivered_at else None
+        })
+
+    return jsonify({
+        'webhook_id': webhook_id,
+        'webhook_name': webhook.name,
+        'logs': logs_data,
+        'total': total,
+        'page': page,
+        'per_page': per_page,
+        'pages': (total + per_page - 1) // per_page
+    })
+
+
+@bp.route('/preview-template', methods=['POST'])
+@api_auth_required
+def preview_template():
+    """
+    Preview a webhook template with sample data.
+
+    Request body:
+        template: Jinja2 template string (required)
+        template_format: Template format - 'json' or 'text' (default: json)
+
+    Returns:
+        JSON response with rendered template preview
+    """
+    data = request.get_json() or {}
+
+    if not data.get('template'):
+        return jsonify({
+            'status': 'error',
+            'message': 'template is required'
+        }), 400
+
+    template = data['template']
+    template_format = data.get('template_format', 'json')
+
+    # Validate template format
+    if template_format not in ['json', 'text']:
+        return jsonify({
+            'status': 'error',
+            'message': 'Invalid template_format. Must be json or text'
+        }), 400
+
+    try:
+        template_service = get_template_service()
+
+        # Validate template
+        is_valid, error_msg = template_service.validate_template(template, template_format)
+        if not is_valid:
+            return jsonify({
+                'status': 'error',
+                'message': f'Template validation error: {error_msg}'
+            }), 400
+
+        # Render with sample data
+        rendered, error = template_service.render_test_payload(template, template_format)
+
+        if error:
+            return jsonify({
+                'status': 'error',
+                'message': f'Template rendering error: {error}'
+            }), 400
+
+        return jsonify({
+            'status': 'success',
+            'rendered': rendered,
+            'format': template_format
+        })
+
+    except Exception as e:
+        return jsonify({
+            'status': 'error',
+            'message': f'Failed to preview template: {str(e)}'
+        }), 500
+
+
+@bp.route('/template-presets', methods=['GET'])
+@api_auth_required
+def get_template_presets():
+    """
+    Get list of available webhook template presets.
+
+    Returns:
+        JSON response with template presets
+    """
+    import os
+
+    try:
+        # Load presets manifest
+        presets_file = os.path.join(
+            os.path.dirname(__file__),
+            '../templates/webhook_presets/presets.json'
+        )
+
+        with open(presets_file, 'r') as f:
+            presets_manifest = json.load(f)
+
+        # Load template contents for each preset
+        presets_dir = os.path.join(
+            os.path.dirname(__file__),
+            '../templates/webhook_presets'
+        )
+
+        for preset in presets_manifest:
+            template_file = os.path.join(presets_dir, preset['file'])
+            with open(template_file, 'r') as f:
+                preset['template'] = f.read()
+            # Remove file reference from response
+            del preset['file']
+
+        return jsonify({
+            'status': 'success',
+            'presets': presets_manifest
+        })
+
+    except FileNotFoundError as e:
+        return jsonify({
+            'status': 'error',
+            'message': f'Template presets not found: {str(e)}'
+        }), 500
+    except Exception as e:
+        return jsonify({
+            'status': 'error',
+            'message': f'Failed to load template presets: {str(e)}'
+        }), 500
+
+
+# Health check endpoint
+@bp.route('/health', methods=['GET'])
+def health_check():
+    """
+    Health check endpoint for monitoring.
+
+    Returns:
+        JSON response with API health status
+    """
+    return jsonify({
+        'status': 'healthy',
+        'api': 'webhooks',
+        'version': '1.0.0-phase5'
+    })

app/web/app.py

@@ -61,7 +61,7 @@ def create_app(config: dict = None) -> Flask:
         SQLALCHEMY_DATABASE_URI=os.environ.get('DATABASE_URL', 'sqlite:///./sneakyscanner.db'),
         SQLALCHEMY_TRACK_MODIFICATIONS=False,
         JSON_SORT_KEYS=False,  # Preserve order in JSON responses
-        MAX_CONTENT_LENGTH=50 * 1024 * 1024,  # 50MB max upload size
+        MAX_CONTENT_LENGTH=50 * 1024 * 1024,  # 50MB max upload size (supports config files up to ~2MB)
     )
 
     # Override with custom config if provided
@@ -95,6 +95,9 @@ def create_app(config: dict = None) -> Flask:
     # Register error handlers
     register_error_handlers(app)
 
+    # Register context processors
+    register_context_processors(app)
+
     # Add request/response handlers
     register_request_handlers(app)
 
@@ -304,9 +307,12 @@ def init_scheduler(app: Flask) -> None:
     with app.app_context():
         # Clean up any orphaned scans from previous crashes/restarts
         scan_service = ScanService(app.db_session)
-        orphaned_count = scan_service.cleanup_orphaned_scans()
-        if orphaned_count > 0:
-            app.logger.warning(f"Cleaned up {orphaned_count} orphaned scan(s) on startup")
+        cleanup_result = scan_service.cleanup_orphaned_scans()
+        if cleanup_result['total'] > 0:
+            app.logger.warning(
+                f"Cleaned up {cleanup_result['total']} orphaned scan(s) on startup: "
+                f"{cleanup_result['recovered']} recovered, {cleanup_result['failed']} failed"
+            )
 
         # Load all enabled schedules from database
         scheduler.load_schedules_on_startup()
@@ -328,10 +334,14 @@ def register_blueprints(app: Flask) -> None:
     from web.api.scans import bp as scans_bp
     from web.api.schedules import bp as schedules_bp
     from web.api.alerts import bp as alerts_bp
+    from web.api.webhooks import bp as webhooks_api_bp
     from web.api.settings import bp as settings_bp
     from web.api.stats import bp as stats_bp
+    from web.api.configs import bp as configs_bp
+    from web.api.sites import bp as sites_bp
     from web.auth.routes import bp as auth_bp
     from web.routes.main import bp as main_bp
+    from web.routes.webhooks import bp as webhooks_bp
 
     # Register authentication blueprint
     app.register_blueprint(auth_bp, url_prefix='/auth')
@@ -339,12 +349,18 @@ def register_blueprints(app: Flask) -> None:
     # Register main web routes blueprint
     app.register_blueprint(main_bp, url_prefix='/')
 
+    # Register webhooks web routes blueprint
+    app.register_blueprint(webhooks_bp, url_prefix='/webhooks')
+
     # Register API blueprints
     app.register_blueprint(scans_bp, url_prefix='/api/scans')
     app.register_blueprint(schedules_bp, url_prefix='/api/schedules')
     app.register_blueprint(alerts_bp, url_prefix='/api/alerts')
+    app.register_blueprint(webhooks_api_bp, url_prefix='/api/webhooks')
     app.register_blueprint(settings_bp, url_prefix='/api/settings')
     app.register_blueprint(stats_bp, url_prefix='/api/stats')
+    app.register_blueprint(configs_bp, url_prefix='/api/configs')
+    app.register_blueprint(sites_bp, url_prefix='/api/sites')
 
     app.logger.info("Blueprints registered")
 
@@ -485,6 +501,35 @@ def register_error_handlers(app: Flask) -> None:
         return render_template('errors/500.html', error=error), 500
 
 
+def register_context_processors(app: Flask) -> None:
+    """
+    Register template context processors.
+
+    Makes common variables available to all templates without having to
+    pass them explicitly in every render_template call.
+
+    Args:
+        app: Flask application instance
+    """
+    @app.context_processor
+    def inject_app_settings():
+        """
+        Inject application metadata into all templates.
+
+        Returns:
+            Dictionary of variables to add to template context
+        """
+        from web.config import APP_NAME, APP_VERSION, REPO_URL
+
+        return {
+            'app_name': APP_NAME,
+            'app_version': APP_VERSION,
+            'repo_url': REPO_URL
+        }
+
+    app.logger.info("Context processors registered")
+
+
 def register_request_handlers(app: Flask) -> None:
     """
     Register request and response handlers.

app/web/config.py

@@ -0,0 +1,16 @@
+"""
+Application configuration and metadata.
+
+Contains version information and other application-level constants
+that are managed by developers, not stored in the database.
+"""
+
+# Application metadata
+APP_NAME = 'SneakyScanner'
+APP_VERSION = '1.0.0-beta'
+
+# Repository URL
+REPO_URL = 'https://git.sneakygeek.net/sneakygeek/SneakyScan'
+
+# Scanner settings
+NMAP_HOST_TIMEOUT = '2m'  # Timeout per host for nmap service detection

app/web/jobs/scan_job.py

@@ -0,0 +1,381 @@
+"""
+Background scan job execution.
+
+This module handles the execution of scans in background threads,
+updating database status and handling errors.
+"""
+
+import json
+import logging
+import threading
+import traceback
+from datetime import datetime
+from pathlib import Path
+
+from sqlalchemy import create_engine
+from sqlalchemy.orm import sessionmaker
+
+from src.scanner import SneakyScanner, ScanCancelledError
+from web.models import Scan, ScanProgress
+from web.services.scan_service import ScanService
+from web.services.alert_service import AlertService
+
+logger = logging.getLogger(__name__)
+
+# Registry for tracking running scanners (scan_id -> SneakyScanner instance)
+_running_scanners = {}
+_running_scanners_lock = threading.Lock()
+
+
+def get_running_scanner(scan_id: int):
+    """Get a running scanner instance by scan ID."""
+    with _running_scanners_lock:
+        return _running_scanners.get(scan_id)
+
+
+def stop_scan(scan_id: int, db_url: str) -> bool:
+    """
+    Stop a running scan.
+
+    Args:
+        scan_id: ID of the scan to stop
+        db_url: Database connection URL
+
+    Returns:
+        True if scan was cancelled, False if not found or already stopped
+    """
+    logger.info(f"Attempting to stop scan {scan_id}")
+
+    # Get the scanner instance
+    scanner = get_running_scanner(scan_id)
+    if not scanner:
+        logger.warning(f"Scanner for scan {scan_id} not found in registry")
+        return False
+
+    # Cancel the scanner
+    scanner.cancel()
+    logger.info(f"Cancellation signal sent to scan {scan_id}")
+
+    return True
+
+
+def create_progress_callback(scan_id: int, session):
+    """
+    Create a progress callback function for updating scan progress in database.
+
+    Args:
+        scan_id: ID of the scan record
+        session: Database session
+
+    Returns:
+        Callback function that accepts (phase, ip, data)
+    """
+    ip_to_site = {}
+
+    def progress_callback(phase: str, ip: str, data: dict):
+        """Update scan progress in database."""
+        nonlocal ip_to_site
+
+        try:
+            # Get scan record
+            scan = session.query(Scan).filter_by(id=scan_id).first()
+            if not scan:
+                return
+
+            # Handle initialization phase
+            if phase == 'init':
+                scan.total_ips = data.get('total_ips', 0)
+                scan.completed_ips = 0
+                scan.current_phase = 'ping'
+                ip_to_site = data.get('ip_to_site', {})
+
+                # Create progress entries for all IPs
+                for ip_addr, site_name in ip_to_site.items():
+                    progress = ScanProgress(
+                        scan_id=scan_id,
+                        ip_address=ip_addr,
+                        site_name=site_name,
+                        phase='pending',
+                        status='pending'
+                    )
+                    session.add(progress)
+
+                session.commit()
+                return
+
+            # Update current phase
+            if data.get('status') == 'starting':
+                scan.current_phase = phase
+                scan.completed_ips = 0
+                session.commit()
+                return
+
+            # Handle phase completion with results
+            if data.get('status') == 'completed':
+                results = data.get('results', {})
+
+                if phase == 'ping':
+                    # Update progress entries with ping results
+                    for ip_addr, ping_result in results.items():
+                        progress = session.query(ScanProgress).filter_by(
+                            scan_id=scan_id, ip_address=ip_addr
+                        ).first()
+                        if progress:
+                            progress.ping_result = ping_result
+                            progress.phase = 'ping'
+                            progress.status = 'completed'
+
+                    scan.completed_ips = len(results)
+
+                elif phase == 'tcp_scan':
+                    # Update progress entries with TCP/UDP port results
+                    for ip_addr, port_data in results.items():
+                        progress = session.query(ScanProgress).filter_by(
+                            scan_id=scan_id, ip_address=ip_addr
+                        ).first()
+                        if progress:
+                            progress.tcp_ports = json.dumps(port_data.get('tcp_ports', []))
+                            progress.udp_ports = json.dumps(port_data.get('udp_ports', []))
+                            progress.phase = 'tcp_scan'
+                            progress.status = 'completed'
+
+                    scan.completed_ips = len(results)
+
+                elif phase == 'service_detection':
+                    # Update progress entries with service detection results
+                    for ip_addr, services in results.items():
+                        progress = session.query(ScanProgress).filter_by(
+                            scan_id=scan_id, ip_address=ip_addr
+                        ).first()
+                        if progress:
+                            # Simplify service data for storage
+                            service_list = []
+                            for svc in services:
+                                service_list.append({
+                                    'port': svc.get('port'),
+                                    'service': svc.get('service', 'unknown'),
+                                    'product': svc.get('product', ''),
+                                    'version': svc.get('version', '')
+                                })
+                            progress.services = json.dumps(service_list)
+                            progress.phase = 'service_detection'
+                            progress.status = 'completed'
+
+                    scan.completed_ips = len(results)
+
+                elif phase == 'http_analysis':
+                    # Mark HTTP analysis as complete
+                    scan.current_phase = 'completed'
+                    scan.completed_ips = scan.total_ips
+
+                session.commit()
+
+        except Exception as e:
+            logger.error(f"Progress callback error for scan {scan_id}: {str(e)}")
+            # Don't re-raise - we don't want to break the scan
+            session.rollback()
+
+    return progress_callback
+
+
+def execute_scan(scan_id: int, config_id: int, db_url: str = None):
+    """
+    Execute a scan in the background.
+
+    This function is designed to run in a background thread via APScheduler.
+    It creates its own database session to avoid conflicts with the main
+    application thread.
+
+    Args:
+        scan_id: ID of the scan record in database
+        config_id: Database config ID
+        db_url: Database connection URL
+
+    Workflow:
+        1. Create new database session for this thread
+        2. Update scan status to 'running'
+        3. Execute scanner
+        4. Generate output files (JSON, HTML, ZIP)
+        5. Save results to database
+        6. Update status to 'completed' or 'failed'
+    """
+    logger.info(f"Starting background scan execution: scan_id={scan_id}, config_id={config_id}")
+
+    # Create new database session for this thread
+    engine = create_engine(db_url, echo=False)
+    Session = sessionmaker(bind=engine)
+    session = Session()
+
+    try:
+        # Get scan record
+        scan = session.query(Scan).filter_by(id=scan_id).first()
+        if not scan:
+            logger.error(f"Scan {scan_id} not found in database")
+            return
+
+        # Update status to running (in case it wasn't already)
+        scan.status = 'running'
+        scan.started_at = datetime.utcnow()
+        session.commit()
+
+        logger.info(f"Scan {scan_id}: Initializing scanner with config_id={config_id}")
+
+        # Initialize scanner with database config
+        scanner = SneakyScanner(config_id=config_id)
+
+        # Register scanner in the running registry
+        with _running_scanners_lock:
+            _running_scanners[scan_id] = scanner
+        logger.debug(f"Scan {scan_id}: Registered in running scanners registry")
+
+        # Create progress callback
+        progress_callback = create_progress_callback(scan_id, session)
+
+        # Execute scan with progress tracking
+        logger.info(f"Scan {scan_id}: Running scanner...")
+        start_time = datetime.utcnow()
+        report, timestamp = scanner.scan(progress_callback=progress_callback)
+        end_time = datetime.utcnow()
+
+        scan_duration = (end_time - start_time).total_seconds()
+        logger.info(f"Scan {scan_id}: Scanner completed in {scan_duration:.2f} seconds")
+
+        # Transition to 'finalizing' status before output generation
+        try:
+            scan = session.query(Scan).filter_by(id=scan_id).first()
+            if scan:
+                scan.status = 'finalizing'
+                scan.current_phase = 'generating_outputs'
+                session.commit()
+                logger.info(f"Scan {scan_id}: Status changed to 'finalizing'")
+        except Exception as e:
+            logger.error(f"Scan {scan_id}: Failed to update status to finalizing: {e}")
+            session.rollback()
+
+        # Generate output files (JSON, HTML, ZIP) with error handling
+        output_paths = {}
+        output_generation_failed = False
+        try:
+            logger.info(f"Scan {scan_id}: Generating output files...")
+            output_paths = scanner.generate_outputs(report, timestamp)
+        except Exception as e:
+            output_generation_failed = True
+            logger.error(f"Scan {scan_id}: Output generation failed: {str(e)}")
+            logger.error(f"Scan {scan_id}: Traceback:\n{traceback.format_exc()}")
+            # Still mark scan as completed with warning since scan data is valid
+            try:
+                scan = session.query(Scan).filter_by(id=scan_id).first()
+                if scan:
+                    scan.status = 'completed'
+                    scan.error_message = f"Scan completed but output file generation failed: {str(e)}"
+                    scan.completed_at = datetime.utcnow()
+                    if scan.started_at:
+                        scan.duration = (datetime.utcnow() - scan.started_at).total_seconds()
+                    session.commit()
+                    logger.info(f"Scan {scan_id}: Marked as completed with output generation warning")
+            except Exception as db_error:
+                logger.error(f"Scan {scan_id}: Failed to update status after output error: {db_error}")
+
+        # Save results to database (only if output generation succeeded)
+        if not output_generation_failed:
+            logger.info(f"Scan {scan_id}: Saving results to database...")
+            scan_service = ScanService(session)
+            scan_service._save_scan_to_db(report, scan_id, status='completed', output_paths=output_paths)
+
+        # Evaluate alert rules
+        logger.info(f"Scan {scan_id}: Evaluating alert rules...")
+        try:
+            alert_service = AlertService(session)
+            alerts_triggered = alert_service.evaluate_alert_rules(scan_id)
+            logger.info(f"Scan {scan_id}: {len(alerts_triggered)} alerts triggered")
+        except Exception as e:
+            # Don't fail the scan if alert evaluation fails
+            logger.error(f"Scan {scan_id}: Alert evaluation failed: {str(e)}")
+            logger.debug(f"Alert evaluation error details: {traceback.format_exc()}")
+
+        logger.info(f"Scan {scan_id}: Completed successfully")
+
+    except ScanCancelledError:
+        # Scan was cancelled by user
+        logger.info(f"Scan {scan_id}: Cancelled by user")
+
+        scan = session.query(Scan).filter_by(id=scan_id).first()
+        if scan:
+            scan.status = 'cancelled'
+            scan.error_message = 'Scan cancelled by user'
+            scan.completed_at = datetime.utcnow()
+            if scan.started_at:
+                scan.duration = (datetime.utcnow() - scan.started_at).total_seconds()
+            session.commit()
+
+    except FileNotFoundError as e:
+        # Config file not found
+        error_msg = f"Configuration file not found: {str(e)}"
+        logger.error(f"Scan {scan_id}: {error_msg}")
+
+        scan = session.query(Scan).filter_by(id=scan_id).first()
+        if scan:
+            scan.status = 'failed'
+            scan.error_message = error_msg
+            scan.completed_at = datetime.utcnow()
+            session.commit()
+
+    except Exception as e:
+        # Any other error during scan execution
+        error_msg = f"Scan execution failed: {str(e)}"
+        logger.error(f"Scan {scan_id}: {error_msg}")
+        logger.error(f"Scan {scan_id}: Traceback:\n{traceback.format_exc()}")
+
+        try:
+            scan = session.query(Scan).filter_by(id=scan_id).first()
+            if scan:
+                scan.status = 'failed'
+                scan.error_message = error_msg
+                scan.completed_at = datetime.utcnow()
+                session.commit()
+        except Exception as db_error:
+            logger.error(f"Scan {scan_id}: Failed to update error status in database: {str(db_error)}")
+
+    finally:
+        # Unregister scanner from registry
+        with _running_scanners_lock:
+            if scan_id in _running_scanners:
+                del _running_scanners[scan_id]
+                logger.debug(f"Scan {scan_id}: Unregistered from running scanners registry")
+
+        # Always close the session
+        session.close()
+        logger.info(f"Scan {scan_id}: Background job completed, session closed")
+
+
+def get_scan_status_from_db(scan_id: int, db_url: str) -> dict:
+    """
+    Helper function to get scan status directly from database.
+
+    Useful for monitoring background jobs without needing Flask app context.
+
+    Args:
+        scan_id: Scan ID to check
+        db_url: Database connection URL
+
+    Returns:
+        Dictionary with scan status information
+    """
+    engine = create_engine(db_url, echo=False)
+    Session = sessionmaker(bind=engine)
+    session = Session()
+
+    try:
+        scan = session.query(Scan).filter_by(id=scan_id).first()
+        if not scan:
+            return None
+
+        return {
+            'scan_id': scan.id,
+            'status': scan.status,
+            'timestamp': scan.timestamp.isoformat() if scan.timestamp else None,
+            'duration': scan.duration,
+            'error_message': scan.error_message
+        }
+    finally:
+        session.close()

app/web/jobs/webhook_job.py

@@ -0,0 +1,59 @@
+"""
+Background webhook delivery job execution.
+
+This module handles the execution of webhook deliveries in background threads,
+updating delivery logs and handling errors.
+"""
+
+import logging
+from sqlalchemy import create_engine
+from sqlalchemy.orm import sessionmaker
+
+from web.services.webhook_service import WebhookService
+
+logger = logging.getLogger(__name__)
+
+
+def execute_webhook_delivery(webhook_id: int, alert_id: int, db_url: str):
+    """
+    Execute a webhook delivery in the background.
+
+    This function is designed to run in a background thread via APScheduler.
+    It creates its own database session to avoid conflicts with the main
+    application thread.
+
+    Args:
+        webhook_id: ID of the webhook to deliver
+        alert_id: ID of the alert to send
+        db_url: Database connection URL
+
+    Workflow:
+        1. Create new database session for this thread
+        2. Call WebhookService to deliver webhook
+        3. WebhookService handles retry logic and logging
+        4. Close session
+    """
+    logger.info(f"Starting background webhook delivery: webhook_id={webhook_id}, alert_id={alert_id}")
+
+    # Create new database session for this thread
+    engine = create_engine(db_url, echo=False)
+    Session = sessionmaker(bind=engine)
+    session = Session()
+
+    try:
+        # Create webhook service and deliver
+        webhook_service = WebhookService(session)
+        success = webhook_service.deliver_webhook(webhook_id, alert_id)
+
+        if success:
+            logger.info(f"Webhook {webhook_id} delivered successfully for alert {alert_id}")
+        else:
+            logger.warning(f"Webhook {webhook_id} delivery failed for alert {alert_id}")
+
+    except Exception as e:
+        logger.error(f"Error during webhook delivery: {e}", exc_info=True)
+
+    finally:
+        session.close()
+        engine.dispose()
+        logger.info(f"Webhook delivery job completed: webhook_id={webhook_id}, alert_id={alert_id}")

app/web/models.py

@@ -45,8 +45,8 @@ class Scan(Base):
     id = Column(Integer, primary_key=True, autoincrement=True)
     timestamp = Column(DateTime, nullable=False, index=True, comment="Scan start time (UTC)")
     duration = Column(Float, nullable=True, comment="Total scan duration in seconds")
-    status = Column(String(20), nullable=False, default='running', comment="running, completed, failed")
-    config_file = Column(Text, nullable=True, comment="Path to YAML config used")
+    status = Column(String(20), nullable=False, default='running', comment="running, finalizing, completed, failed, cancelled")
+    config_id = Column(Integer, ForeignKey('scan_configs.id'), nullable=True, index=True, comment="FK to scan_configs table")
     title = Column(Text, nullable=True, comment="Scan title from config")
     json_path = Column(Text, nullable=True, comment="Path to JSON report")
     html_path = Column(Text, nullable=True, comment="Path to HTML report")
@@ -59,6 +59,11 @@ class Scan(Base):
     completed_at = Column(DateTime, nullable=True, comment="Scan execution completion time")
     error_message = Column(Text, nullable=True, comment="Error message if scan failed")
 
+    # Progress tracking fields
+    current_phase = Column(String(50), nullable=True, comment="Current scan phase: ping, tcp_scan, udp_scan, service_detection, http_analysis")
+    total_ips = Column(Integer, nullable=True, comment="Total number of IPs to scan")
+    completed_ips = Column(Integer, nullable=True, default=0, comment="Number of IPs completed in current phase")
+
     # Relationships
     sites = relationship('ScanSite', back_populates='scan', cascade='all, delete-orphan')
     ips = relationship('ScanIP', back_populates='scan', cascade='all, delete-orphan')
@@ -68,6 +73,9 @@ class Scan(Base):
     tls_versions = relationship('ScanTLSVersion', back_populates='scan', cascade='all, delete-orphan')
     alerts = relationship('Alert', back_populates='scan', cascade='all, delete-orphan')
     schedule = relationship('Schedule', back_populates='scans')
+    config = relationship('ScanConfig', back_populates='scans')
+    site_associations = relationship('ScanSiteAssociation', back_populates='scan', cascade='all, delete-orphan')
+    progress_entries = relationship('ScanProgress', back_populates='scan', cascade='all, delete-orphan')
 
     def __repr__(self):
         return f"<Scan(id={self.id}, title='{self.title}', status='{self.status}')>"
@@ -242,6 +250,185 @@ class ScanTLSVersion(Base):
         return f"<ScanTLSVersion(id={self.id}, tls_version='{self.tls_version}', supported={self.supported})>"
 
 
+class ScanProgress(Base):
+    """
+    Real-time progress tracking for individual IPs during scan execution.
+
+    Stores intermediate results as they become available, allowing users to
+    see progress and results before the full scan completes.
+    """
+    __tablename__ = 'scan_progress'
+
+    id = Column(Integer, primary_key=True, autoincrement=True)
+    scan_id = Column(Integer, ForeignKey('scans.id'), nullable=False, index=True)
+    ip_address = Column(String(45), nullable=False, comment="IP address being scanned")
+    site_name = Column(String(255), nullable=True, comment="Site name this IP belongs to")
+    phase = Column(String(50), nullable=False, comment="Phase: ping, tcp_scan, udp_scan, service_detection, http_analysis")
+    status = Column(String(20), nullable=False, default='pending', comment="pending, in_progress, completed, failed")
+
+    # Results data (stored as JSON)
+    ping_result = Column(Boolean, nullable=True, comment="Ping response result")
+    tcp_ports = Column(Text, nullable=True, comment="JSON array of discovered TCP ports")
+    udp_ports = Column(Text, nullable=True, comment="JSON array of discovered UDP ports")
+    services = Column(Text, nullable=True, comment="JSON array of detected services")
+
+    created_at = Column(DateTime, nullable=False, default=datetime.utcnow, comment="Entry creation time")
+    updated_at = Column(DateTime, nullable=False, default=datetime.utcnow, onupdate=datetime.utcnow, comment="Last update time")
+
+    # Relationships
+    scan = relationship('Scan', back_populates='progress_entries')
+
+    # Index for efficient lookups
+    __table_args__ = (
+        UniqueConstraint('scan_id', 'ip_address', name='uix_scan_progress_ip'),
+    )
+
+    def __repr__(self):
+        return f"<ScanProgress(id={self.id}, ip='{self.ip_address}', phase='{self.phase}', status='{self.status}')>"
+
+
+# ============================================================================
+# Reusable Site Definition Tables
+# ============================================================================
+
+
+class Site(Base):
+    """
+    Master site definition (reusable across scans).
+
+    Sites represent logical network segments (e.g., "Production DC", "DMZ",
+    "Branch Office") that can be reused across multiple scans. Each site
+    contains one or more CIDR ranges.
+    """
+    __tablename__ = 'sites'
+
+    id = Column(Integer, primary_key=True, autoincrement=True)
+    name = Column(String(255), nullable=False, unique=True, index=True, comment="Unique site name")
+    description = Column(Text, nullable=True, comment="Site description")
+    created_at = Column(DateTime, nullable=False, default=datetime.utcnow, comment="Site creation time")
+    updated_at = Column(DateTime, nullable=False, default=datetime.utcnow, onupdate=datetime.utcnow, comment="Last modification time")
+
+    # Relationships
+    ips = relationship('SiteIP', back_populates='site', cascade='all, delete-orphan')
+    scan_associations = relationship('ScanSiteAssociation', back_populates='site')
+    config_associations = relationship('ScanConfigSite', back_populates='site')
+
+    def __repr__(self):
+        return f"<Site(id={self.id}, name='{self.name}')>"
+
+
+class SiteIP(Base):
+    """
+    Individual IP addresses with their own settings.
+
+    Each IP is directly associated with a site and has its own port and ping settings.
+    IPs are standalone entities - CIDRs are only used as a convenience for bulk creation.
+    """
+    __tablename__ = 'site_ips'
+
+    id = Column(Integer, primary_key=True, autoincrement=True)
+    site_id = Column(Integer, ForeignKey('sites.id'), nullable=False, index=True, comment="FK to sites")
+    ip_address = Column(String(45), nullable=False, comment="IPv4 or IPv6 address")
+    expected_ping = Column(Boolean, nullable=True, comment="Expected ping response for this IP")
+    expected_tcp_ports = Column(Text, nullable=True, comment="JSON array of expected TCP ports")
+    expected_udp_ports = Column(Text, nullable=True, comment="JSON array of expected UDP ports")
+    created_at = Column(DateTime, nullable=False, default=datetime.utcnow, comment="IP creation time")
+
+    # Relationships
+    site = relationship('Site', back_populates='ips')
+
+    # Index for efficient IP lookups - prevent duplicate IPs within a site
+    __table_args__ = (
+        UniqueConstraint('site_id', 'ip_address', name='uix_site_ip_address'),
+    )
+
+    def __repr__(self):
+        return f"<SiteIP(id={self.id}, ip_address='{self.ip_address}')>"
+
+
+class ScanSiteAssociation(Base):
+    """
+    Many-to-many relationship between scans and sites.
+
+    Tracks which sites were included in which scans. This allows sites
+    to be reused across multiple scans.
+    """
+    __tablename__ = 'scan_site_associations'
+
+    id = Column(Integer, primary_key=True, autoincrement=True)
+    scan_id = Column(Integer, ForeignKey('scans.id'), nullable=False, index=True)
+    site_id = Column(Integer, ForeignKey('sites.id'), nullable=False, index=True)
+    created_at = Column(DateTime, nullable=False, default=datetime.utcnow, comment="Association creation time")
+
+    # Relationships
+    scan = relationship('Scan', back_populates='site_associations')
+    site = relationship('Site', back_populates='scan_associations')
+
+    # Index to prevent duplicate associations
+    __table_args__ = (
+        UniqueConstraint('scan_id', 'site_id', name='uix_scan_site'),
+    )
+
+    def __repr__(self):
+        return f"<ScanSiteAssociation(scan_id={self.scan_id}, site_id={self.site_id})>"
+
+
+# ============================================================================
+# Scan Configuration Tables
+# ============================================================================
+
+
+class ScanConfig(Base):
+    """
+    Scan configurations stored in database (replaces YAML files).
+
+    Stores reusable scan configurations that reference sites from the
+    sites table. Configs define what sites to scan together.
+    """
+    __tablename__ = 'scan_configs'
+
+    id = Column(Integer, primary_key=True, autoincrement=True)
+    title = Column(String(255), nullable=False, comment="Configuration title")
+    description = Column(Text, nullable=True, comment="Configuration description")
+    created_at = Column(DateTime, nullable=False, default=datetime.utcnow, comment="Config creation time")
+    updated_at = Column(DateTime, nullable=False, default=datetime.utcnow, onupdate=datetime.utcnow, comment="Last modification time")
+
+    # Relationships
+    site_associations = relationship('ScanConfigSite', back_populates='config', cascade='all, delete-orphan')
+    scans = relationship('Scan', back_populates='config')
+    schedules = relationship('Schedule', back_populates='config')
+
+    def __repr__(self):
+        return f"<ScanConfig(id={self.id}, title='{self.title}')>"
+
+
+class ScanConfigSite(Base):
+    """
+    Many-to-many relationship between scan configs and sites.
+
+    Links scan configurations to the sites they should scan. A config
+    can reference multiple sites, and sites can be used in multiple configs.
+    """
+    __tablename__ = 'scan_config_sites'
+
+    id = Column(Integer, primary_key=True, autoincrement=True)
+    config_id = Column(Integer, ForeignKey('scan_configs.id'), nullable=False, index=True)
+    site_id = Column(Integer, ForeignKey('sites.id'), nullable=False, index=True)
+    created_at = Column(DateTime, nullable=False, default=datetime.utcnow, comment="Association creation time")
+
+    # Relationships
+    config = relationship('ScanConfig', back_populates='site_associations')
+    site = relationship('Site', back_populates='config_associations')
+
+    # Index to prevent duplicate associations
+    __table_args__ = (
+        UniqueConstraint('config_id', 'site_id', name='uix_config_site'),
+    )
+
+    def __repr__(self):
+        return f"<ScanConfigSite(config_id={self.config_id}, site_id={self.site_id})>"
+
+
 # ============================================================================
 # Scheduling & Notifications Tables
 # ============================================================================
@@ -258,7 +445,7 @@ class Schedule(Base):
 
     id = Column(Integer, primary_key=True, autoincrement=True)
     name = Column(String(255), nullable=False, comment="Schedule name (e.g., 'Daily prod scan')")
-    config_file = Column(Text, nullable=False, comment="Path to YAML config")
+    config_id = Column(Integer, ForeignKey('scan_configs.id'), nullable=True, index=True, comment="FK to scan_configs table")
     cron_expression = Column(String(100), nullable=False, comment="Cron-like schedule (e.g., '0 2 * * *')")
     enabled = Column(Boolean, nullable=False, default=True, comment="Is schedule active?")
     last_run = Column(DateTime, nullable=True, comment="Last execution time")
@@ -268,6 +455,7 @@ class Schedule(Base):
 
     # Relationships
     scans = relationship('Scan', back_populates='schedule')
+    config = relationship('ScanConfig', back_populates='schedules')
 
     def __repr__(self):
         return f"<Schedule(id={self.id}, name='{self.name}', enabled={self.enabled})>"
@@ -284,17 +472,24 @@ class Alert(Base):
 
     id = Column(Integer, primary_key=True, autoincrement=True)
     scan_id = Column(Integer, ForeignKey('scans.id'), nullable=False, index=True)
-    alert_type = Column(String(50), nullable=False, comment="new_port, cert_expiry, service_change, ping_failed")
+    rule_id = Column(Integer, ForeignKey('alert_rules.id'), nullable=True, index=True, comment="Associated alert rule")
+    alert_type = Column(String(50), nullable=False, comment="unexpected_port, drift_detection, cert_expiry, service_change, ping_failed")
     severity = Column(String(20), nullable=False, comment="info, warning, critical")
     message = Column(Text, nullable=False, comment="Human-readable alert message")
     ip_address = Column(String(45), nullable=True, comment="Related IP (optional)")
     port = Column(Integer, nullable=True, comment="Related port (optional)")
     email_sent = Column(Boolean, nullable=False, default=False, comment="Was email notification sent?")
     email_sent_at = Column(DateTime, nullable=True, comment="Email send timestamp")
+    webhook_sent = Column(Boolean, nullable=False, default=False, comment="Was webhook sent?")
+    webhook_sent_at = Column(DateTime, nullable=True, comment="Webhook send timestamp")
+    acknowledged = Column(Boolean, nullable=False, default=False, index=True, comment="Was alert acknowledged?")
+    acknowledged_at = Column(DateTime, nullable=True, comment="Acknowledgment timestamp")
+    acknowledged_by = Column(String(255), nullable=True, comment="User who acknowledged")
     created_at = Column(DateTime, nullable=False, default=datetime.utcnow, comment="Alert creation time")
 
     # Relationships
     scan = relationship('Scan', back_populates='alerts')
+    rule = relationship('AlertRule', back_populates='alerts')
 
     # Index for alert queries by type and severity
     __table_args__ = (
@@ -315,14 +510,83 @@ class AlertRule(Base):
     __tablename__ = 'alert_rules'
 
     id = Column(Integer, primary_key=True, autoincrement=True)
-    rule_type = Column(String(50), nullable=False, comment="unexpected_port, cert_expiry, service_down, etc.")
+    name = Column(String(255), nullable=True, comment="User-friendly rule name")
+    rule_type = Column(String(50), nullable=False, comment="unexpected_port, cert_expiry, service_down, drift_detection, etc.")
     enabled = Column(Boolean, nullable=False, default=True, comment="Is rule active?")
     threshold = Column(Integer, nullable=True, comment="Threshold value (e.g., days for cert expiry)")
     email_enabled = Column(Boolean, nullable=False, default=False, comment="Send email for this rule?")
+    webhook_enabled = Column(Boolean, nullable=False, default=False, comment="Send webhook for this rule?")
+    severity = Column(String(20), nullable=True, comment="Alert severity: critical, warning, info")
+    filter_conditions = Column(Text, nullable=True, comment="JSON filter conditions for the rule")
+    config_id = Column(Integer, ForeignKey('scan_configs.id'), nullable=True, index=True, comment="Optional: specific config this rule applies to")
     created_at = Column(DateTime, nullable=False, default=datetime.utcnow, comment="Rule creation time")
+    updated_at = Column(DateTime, nullable=True, comment="Last update time")
+
+    # Relationships
+    alerts = relationship("Alert", back_populates="rule", cascade="all, delete-orphan")
+    config = relationship("ScanConfig", backref="alert_rules")
 
     def __repr__(self):
-        return f"<AlertRule(id={self.id}, rule_type='{self.rule_type}', enabled={self.enabled})>"
+        return f"<AlertRule(id={self.id}, name='{self.name}', rule_type='{self.rule_type}', enabled={self.enabled})>"
+
+
+class Webhook(Base):
+    """
+    Webhook configurations for alert notifications.
+
+    Stores webhook endpoints and authentication details for sending alert
+    notifications to external systems.
+    """
+    __tablename__ = 'webhooks'
+
+    id = Column(Integer, primary_key=True, autoincrement=True)
+    name = Column(String(255), nullable=False, comment="Webhook name")
+    url = Column(Text, nullable=False, comment="Webhook URL")
+    enabled = Column(Boolean, nullable=False, default=True, comment="Is webhook enabled?")
+    auth_type = Column(String(20), nullable=True, comment="Authentication type: none, bearer, basic, custom")
+    auth_token = Column(Text, nullable=True, comment="Encrypted authentication token")
+    custom_headers = Column(Text, nullable=True, comment="JSON custom headers")
+    alert_types = Column(Text, nullable=True, comment="JSON array of alert types to trigger on")
+    severity_filter = Column(Text, nullable=True, comment="JSON array of severities to trigger on")
+    timeout = Column(Integer, nullable=True, default=10, comment="Request timeout in seconds")
+    retry_count = Column(Integer, nullable=True, default=3, comment="Number of retry attempts")
+    template = Column(Text, nullable=True, comment="Jinja2 template for webhook payload")
+    template_format = Column(String(20), nullable=True, default='json', comment="Template output format: json, text")
+    content_type_override = Column(String(100), nullable=True, comment="Optional custom Content-Type header")
+    created_at = Column(DateTime, nullable=False, default=datetime.utcnow, comment="Creation time")
+    updated_at = Column(DateTime, nullable=False, default=datetime.utcnow, comment="Last update time")
+
+    # Relationships
+    delivery_logs = relationship("WebhookDeliveryLog", back_populates="webhook", cascade="all, delete-orphan")
+
+    def __repr__(self):
+        return f"<Webhook(id={self.id}, name='{self.name}', enabled={self.enabled})>"
+
+
+class WebhookDeliveryLog(Base):
+    """
+    Webhook delivery tracking.
+
+    Logs all webhook delivery attempts for auditing and debugging purposes.
+    """
+    __tablename__ = 'webhook_delivery_log'
+
+    id = Column(Integer, primary_key=True, autoincrement=True)
+    webhook_id = Column(Integer, ForeignKey('webhooks.id'), nullable=False, index=True, comment="Associated webhook")
+    alert_id = Column(Integer, ForeignKey('alerts.id'), nullable=False, index=True, comment="Associated alert")
+    status = Column(String(20), nullable=True, index=True, comment="Delivery status: success, failed, retrying")
+    response_code = Column(Integer, nullable=True, comment="HTTP response code")
+    response_body = Column(Text, nullable=True, comment="Response body from webhook")
+    error_message = Column(Text, nullable=True, comment="Error message if failed")
+    attempt_number = Column(Integer, nullable=True, comment="Which attempt this was")
+    delivered_at = Column(DateTime, nullable=False, default=datetime.utcnow, comment="Delivery timestamp")
+
+    # Relationships
+    webhook = relationship("Webhook", back_populates="delivery_logs")
+    alert = relationship("Alert")
+
+    def __repr__(self):
+        return f"<WebhookDeliveryLog(id={self.id}, webhook_id={self.webhook_id}, status='{self.status}')>"
 
 
 # ============================================================================

app/web/routes/main.py

@@ -0,0 +1,288 @@
+"""
+Main web routes for SneakyScanner.
+
+Provides dashboard and scan viewing pages.
+"""
+
+import logging
+import os
+
+from flask import Blueprint, current_app, redirect, render_template, request, send_from_directory, url_for
+
+from web.auth.decorators import login_required
+
+logger = logging.getLogger(__name__)
+
+bp = Blueprint('main', __name__)
+
+
+@bp.route('/')
+def index():
+    """
+    Root route - redirect to dashboard.
+
+    Returns:
+        Redirect to dashboard
+    """
+    return redirect(url_for('main.dashboard'))
+
+
+@bp.route('/dashboard')
+@login_required
+def dashboard():
+    """
+    Dashboard page - shows recent scans and statistics.
+
+    Returns:
+        Rendered dashboard template
+    """
+    return render_template('dashboard.html')
+
+
+@bp.route('/scans')
+@login_required
+def scans():
+    """
+    Scans list page - shows all scans with pagination.
+
+    Returns:
+        Rendered scans list template
+    """
+    return render_template('scans.html')
+
+
+@bp.route('/scans/<int:scan_id>')
+@login_required
+def scan_detail(scan_id):
+    """
+    Scan detail page - shows full scan results.
+
+    Args:
+        scan_id: Scan ID to display
+
+    Returns:
+        Rendered scan detail template
+    """
+    # TODO: Phase 5 - Implement scan detail page
+    return render_template('scan_detail.html', scan_id=scan_id)
+
+
+@bp.route('/scans/<int:scan_id1>/compare/<int:scan_id2>')
+@login_required
+def compare_scans(scan_id1, scan_id2):
+    """
+    Scan comparison page - shows differences between two scans.
+
+    Args:
+        scan_id1: First (older) scan ID
+        scan_id2: Second (newer) scan ID
+
+    Returns:
+        Rendered comparison template
+    """
+    return render_template('scan_compare.html', scan_id1=scan_id1, scan_id2=scan_id2)
+
+
+@bp.route('/search/ip')
+@login_required
+def search_ip():
+    """
+    IP search results page - shows scans containing a specific IP address.
+
+    Returns:
+        Rendered search results template
+    """
+    ip_address = request.args.get('ip', '').strip()
+    return render_template('ip_search_results.html', ip_address=ip_address)
+
+
+@bp.route('/schedules')
+@login_required
+def schedules():
+    """
+    Schedules list page - shows all scheduled scans.
+
+    Returns:
+        Rendered schedules list template
+    """
+    return render_template('schedules.html')
+
+
+@bp.route('/schedules/create')
+@login_required
+def create_schedule():
+    """
+    Create new schedule form page.
+
+    Returns:
+        Rendered schedule create template with available configs
+    """
+    from web.models import ScanConfig
+
+    # Get list of available configs from database
+    configs = []
+
+    try:
+        configs = current_app.db_session.query(ScanConfig).order_by(ScanConfig.title).all()
+    except Exception as e:
+        logger.error(f"Error listing configs: {e}")
+
+    return render_template('schedule_create.html', configs=configs)
+
+
+@bp.route('/schedules/<int:schedule_id>/edit')
+@login_required
+def edit_schedule(schedule_id):
+    """
+    Edit existing schedule form page.
+
+    Args:
+        schedule_id: Schedule ID to edit
+
+    Returns:
+        Rendered schedule edit template
+    """
+    # Note: Schedule data is loaded via AJAX in the template
+    # This just renders the page with the schedule_id in the URL
+    return render_template('schedule_edit.html', schedule_id=schedule_id)
+
+
+@bp.route('/sites')
+@login_required
+def sites():
+    """
+    Sites management page - manage reusable site definitions.
+
+    Returns:
+        Rendered sites template
+    """
+    return render_template('sites.html')
+
+
+@bp.route('/configs')
+@login_required
+def configs():
+    """
+    Configuration files list page - shows all config files.
+
+    Returns:
+        Rendered configs list template
+    """
+    return render_template('configs.html')
+
+
+@bp.route('/alerts')
+@login_required
+def alerts():
+    """
+    Alerts history page - shows all alerts.
+
+    Returns:
+        Rendered alerts template
+    """
+    from flask import request, current_app
+    from web.models import Alert, AlertRule, Scan
+    from web.utils.pagination import paginate
+
+    # Get query parameters for filtering
+    page = request.args.get('page', 1, type=int)
+    per_page = 20
+    severity = request.args.get('severity')
+    alert_type = request.args.get('alert_type')
+    acknowledged = request.args.get('acknowledged')
+
+    # Build query
+    query = current_app.db_session.query(Alert).join(Scan, isouter=True)
+
+    # Apply filters
+    if severity:
+        query = query.filter(Alert.severity == severity)
+    if alert_type:
+        query = query.filter(Alert.alert_type == alert_type)
+    if acknowledged is not None:
+        ack_bool = acknowledged == 'true'
+        query = query.filter(Alert.acknowledged == ack_bool)
+
+    # Order by severity and date
+    query = query.order_by(Alert.severity.desc(), Alert.created_at.desc())
+
+    # Paginate using utility function
+    pagination = paginate(query, page=page, per_page=per_page)
+    alerts = pagination.items
+
+    # Get unique alert types for filter dropdown
+    try:
+        alert_types = current_app.db_session.query(Alert.alert_type).distinct().all()
+        alert_types = [at[0] for at in alert_types] if alert_types else []
+    except Exception:
+        alert_types = []
+
+    return render_template(
+        'alerts.html',
+        alerts=alerts,
+        pagination=pagination,
+        current_severity=severity,
+        current_alert_type=alert_type,
+        current_acknowledged=acknowledged,
+        alert_types=alert_types
+    )
+
+
+@bp.route('/alerts/rules')
+@login_required
+def alert_rules():
+    """
+    Alert rules management page.
+
+    Returns:
+        Rendered alert rules template
+    """
+    from flask import current_app
+    from web.models import AlertRule
+
+    # Get all alert rules with error handling
+    try:
+        rules = current_app.db_session.query(AlertRule).order_by(
+            AlertRule.name.nullslast(),
+            AlertRule.rule_type
+        ).all()
+    except Exception as e:
+        logger.error(f"Error fetching alert rules: {e}")
+        rules = []
+
+    # Ensure rules is always a list
+    if rules is None:
+        rules = []
+
+    return render_template(
+        'alert_rules.html',
+        rules=rules
+    )
+
+
+@bp.route('/help')
+@login_required
+def help():
+    """
+    Help page - explains how to use the application.
+
+    Returns:
+        Rendered help template
+    """
+    return render_template('help.html')
+
+
+@bp.route('/output/<path:filename>')
+@login_required
+def serve_output_file(filename):
+    """
+    Serve output files (JSON, HTML, ZIP) from the output directory.
+
+    Args:
+        filename: Name of the file to serve
+
+    Returns:
+        The requested file
+    """
+    output_dir = os.environ.get('OUTPUT_DIR', '/app/output')
+    return send_from_directory(output_dir, filename)

app/web/routes/webhooks.py

@@ -0,0 +1,83 @@
+"""
+Webhook web routes for SneakyScanner.
+
+Provides UI pages for managing webhooks and viewing delivery logs.
+"""
+
+import logging
+
+from flask import Blueprint, render_template, request, redirect, url_for, flash, current_app
+
+from web.auth.decorators import login_required
+from web.models import Webhook
+from web.services.webhook_service import WebhookService
+
+logger = logging.getLogger(__name__)
+
+bp = Blueprint('webhooks', __name__)
+
+
+@bp.route('')
+@login_required
+def list_webhooks():
+    """
+    Webhooks list page - shows all configured webhooks.
+
+    Returns:
+        Rendered webhooks list template
+    """
+    return render_template('webhooks/list.html')
+
+
+@bp.route('/new')
+@login_required
+def new_webhook():
+    """
+    New webhook form page.
+
+    Returns:
+        Rendered webhook form template
+    """
+    return render_template('webhooks/form.html', webhook=None, mode='create')
+
+
+@bp.route('/<int:webhook_id>/edit')
+@login_required
+def edit_webhook(webhook_id):
+    """
+    Edit webhook form page.
+
+    Args:
+        webhook_id: Webhook ID to edit
+
+    Returns:
+        Rendered webhook form template or 404
+    """
+    webhook = current_app.db_session.query(Webhook).filter(Webhook.id == webhook_id).first()
+
+    if not webhook:
+        flash('Webhook not found', 'error')
+        return redirect(url_for('webhooks.list_webhooks'))
+
+    return render_template('webhooks/form.html', webhook=webhook, mode='edit')
+
+
+@bp.route('/<int:webhook_id>/logs')
+@login_required
+def webhook_logs(webhook_id):
+    """
+    Webhook delivery logs page.
+
+    Args:
+        webhook_id: Webhook ID
+
+    Returns:
+        Rendered webhook logs template or 404
+    """
+    webhook = current_app.db_session.query(Webhook).filter(Webhook.id == webhook_id).first()
+
+    if not webhook:
+        flash('Webhook not found', 'error')
+        return redirect(url_for('webhooks.list_webhooks'))
+
+    return render_template('webhooks/logs.html', webhook=webhook)

app/web/services/alert_service.py

@@ -0,0 +1,521 @@
+"""
+Alert Service Module
+
+Handles alert evaluation, rule processing, and notification triggering
+for SneakyScan Phase 5.
+"""
+import logging
+from datetime import datetime, timezone
+from typing import List, Dict, Optional, Any
+from sqlalchemy.orm import Session
+
+from ..models import (
+    Alert, AlertRule, Scan, ScanPort, ScanIP, ScanService as ScanServiceModel,
+    ScanCertificate, ScanTLSVersion
+)
+from .scan_service import ScanService
+
+logger = logging.getLogger(__name__)
+
+
+class AlertService:
+    """
+    Service for evaluating alert rules and generating alerts based on scan results.
+
+    Supports two main alert types:
+    1. Unexpected Port Detection - Alerts when ports marked as unexpected are found open
+    2. Drift Detection - Alerts when scan results differ from previous scan
+    """
+
+    def __init__(self, db_session: Session):
+        self.db = db_session
+        self.scan_service = ScanService(db_session)
+
+    def evaluate_alert_rules(self, scan_id: int) -> List[Alert]:
+        """
+        Main entry point for alert evaluation after scan completion.
+
+        Args:
+            scan_id: ID of the completed scan to evaluate
+
+        Returns:
+            List of Alert objects that were created
+        """
+        logger.info(f"Starting alert evaluation for scan {scan_id}")
+
+        # Get the scan
+        scan = self.db.query(Scan).filter(Scan.id == scan_id).first()
+        if not scan:
+            logger.error(f"Scan {scan_id} not found")
+            return []
+
+        # Get all enabled alert rules
+        rules = self.db.query(AlertRule).filter(AlertRule.enabled == True).all()
+        logger.info(f"Found {len(rules)} enabled alert rules to evaluate")
+
+        alerts_created = []
+
+        for rule in rules:
+            try:
+                # Check if rule applies to this scan's config
+                if rule.config_id and scan.config_id != rule.config_id:
+                    logger.debug(f"Skipping rule {rule.id} - config mismatch")
+                    continue
+
+                # Evaluate based on rule type
+                alert_data = []
+
+                if rule.rule_type == 'unexpected_port':
+                    alert_data = self.check_unexpected_ports(scan, rule)
+                elif rule.rule_type == 'drift_detection':
+                    alert_data = self.check_drift_from_previous(scan, rule)
+                elif rule.rule_type == 'cert_expiry':
+                    alert_data = self.check_certificate_expiry(scan, rule)
+                elif rule.rule_type == 'weak_tls':
+                    alert_data = self.check_weak_tls(scan, rule)
+                elif rule.rule_type == 'ping_failed':
+                    alert_data = self.check_ping_failures(scan, rule)
+                else:
+                    logger.warning(f"Unknown rule type: {rule.rule_type}")
+                    continue
+
+                # Create alerts for any findings
+                for alert_info in alert_data:
+                    alert = self.create_alert(scan_id, rule, alert_info)
+                    if alert:
+                        alerts_created.append(alert)
+
+                        # Trigger notifications if configured
+                        if rule.email_enabled or rule.webhook_enabled:
+                            self.trigger_notifications(alert, rule)
+
+                logger.info(f"Rule {rule.name or rule.id} generated {len(alert_data)} alerts")
+
+            except Exception as e:
+                logger.error(f"Error evaluating rule {rule.id}: {str(e)}")
+                continue
+
+        logger.info(f"Alert evaluation complete. Created {len(alerts_created)} alerts")
+        return alerts_created
+
+    def check_unexpected_ports(self, scan: Scan, rule: AlertRule) -> List[Dict[str, Any]]:
+        """
+        Detect ports that are open but not in the expected_ports list.
+
+        Args:
+            scan: The scan to check
+            rule: The alert rule configuration
+
+        Returns:
+            List of alert data dictionaries
+        """
+        alerts_to_create = []
+
+        # Get all ports where expected=False
+        unexpected_ports = (
+            self.db.query(ScanPort, ScanIP)
+            .join(ScanIP, ScanPort.ip_id == ScanIP.id)
+            .filter(ScanPort.scan_id == scan.id)
+            .filter(ScanPort.expected == False)  # Not in config's expected_ports
+            .filter(ScanPort.state == 'open')
+            .all()
+        )
+
+        # High-risk ports that should trigger critical alerts
+        high_risk_ports = {
+            22,    # SSH
+            23,    # Telnet
+            135,   # Windows RPC
+            139,   # NetBIOS
+            445,   # SMB
+            1433,  # SQL Server
+            3306,  # MySQL
+            3389,  # RDP
+            5432,  # PostgreSQL
+            5900,  # VNC
+            6379,  # Redis
+            9200,  # Elasticsearch
+            27017, # MongoDB
+        }
+
+        for port, ip in unexpected_ports:
+            # Determine severity based on port number
+            severity = rule.severity or ('critical' if port.port in high_risk_ports else 'warning')
+
+            # Get service info if available
+            service = (
+                self.db.query(ScanServiceModel)
+                .filter(ScanServiceModel.port_id == port.id)
+                .first()
+            )
+
+            service_info = ""
+            if service:
+                product = service.product or "Unknown"
+                version = service.version or ""
+                service_info = f" (Service: {service.service_name}: {product} {version}".strip() + ")"
+
+            alerts_to_create.append({
+                'alert_type': 'unexpected_port',
+                'severity': severity,
+                'message': f"Unexpected port open on {ip.ip_address}:{port.port}/{port.protocol}{service_info}",
+                'ip_address': ip.ip_address,
+                'port': port.port
+            })
+
+        return alerts_to_create
+
+    def check_drift_from_previous(self, scan: Scan, rule: AlertRule) -> List[Dict[str, Any]]:
+        """
+        Compare current scan to the last scan with the same config.
+
+        Args:
+            scan: The current scan
+            rule: The alert rule configuration
+
+        Returns:
+            List of alert data dictionaries
+        """
+        alerts_to_create = []
+
+        # Find previous scan with same config_id
+        previous_scan = (
+            self.db.query(Scan)
+            .filter(Scan.config_id == scan.config_id)
+            .filter(Scan.id < scan.id)
+            .filter(Scan.status == 'completed')
+            .order_by(Scan.started_at.desc() if Scan.started_at else Scan.timestamp.desc())
+            .first()
+        )
+
+        if not previous_scan:
+            logger.info(f"No previous scan found for config_id {scan.config_id}")
+            return []
+
+        try:
+            # Use existing comparison logic from scan_service
+            comparison = self.scan_service.compare_scans(previous_scan.id, scan.id)
+
+            # Alert on new ports
+            for port_data in comparison.get('ports', {}).get('added', []):
+                severity = rule.severity or 'warning'
+                alerts_to_create.append({
+                    'alert_type': 'drift_new_port',
+                    'severity': severity,
+                    'message': f"New port detected: {port_data['ip']}:{port_data['port']}/{port_data['protocol']}",
+                    'ip_address': port_data['ip'],
+                    'port': port_data['port']
+                })
+
+            # Alert on removed ports
+            for port_data in comparison.get('ports', {}).get('removed', []):
+                severity = rule.severity or 'info'
+                alerts_to_create.append({
+                    'alert_type': 'drift_missing_port',
+                    'severity': severity,
+                    'message': f"Port no longer open: {port_data['ip']}:{port_data['port']}/{port_data['protocol']}",
+                    'ip_address': port_data['ip'],
+                    'port': port_data['port']
+                })
+
+            # Alert on service changes
+            for svc_data in comparison.get('services', {}).get('changed', []):
+                old_svc = svc_data.get('old', {})
+                new_svc = svc_data.get('new', {})
+
+                old_desc = f"{old_svc.get('product', 'Unknown')} {old_svc.get('version', '')}".strip()
+                new_desc = f"{new_svc.get('product', 'Unknown')} {new_svc.get('version', '')}".strip()
+
+                severity = rule.severity or 'info'
+                alerts_to_create.append({
+                    'alert_type': 'drift_service_change',
+                    'severity': severity,
+                    'message': f"Service changed on {svc_data['ip']}:{svc_data['port']}: {old_desc} → {new_desc}",
+                    'ip_address': svc_data['ip'],
+                    'port': svc_data['port']
+                })
+
+            # Alert on certificate changes
+            for cert_data in comparison.get('certificates', {}).get('changed', []):
+                old_cert = cert_data.get('old', {})
+                new_cert = cert_data.get('new', {})
+
+                severity = rule.severity or 'warning'
+                alerts_to_create.append({
+                    'alert_type': 'drift_cert_change',
+                    'severity': severity,
+                    'message': f"Certificate changed on {cert_data['ip']}:{cert_data['port']} - "
+                              f"Subject: {old_cert.get('subject', 'Unknown')} → {new_cert.get('subject', 'Unknown')}",
+                    'ip_address': cert_data['ip'],
+                    'port': cert_data['port']
+                })
+
+            # Check drift score threshold if configured
+            if rule.threshold and comparison.get('drift_score', 0) * 100 >= rule.threshold:
+                alerts_to_create.append({
+                    'alert_type': 'drift_threshold_exceeded',
+                    'severity': rule.severity or 'warning',
+                    'message': f"Drift score {comparison['drift_score']*100:.1f}% exceeds threshold {rule.threshold}%",
+                    'ip_address': None,
+                    'port': None
+                })
+
+        except Exception as e:
+            logger.error(f"Error comparing scans: {str(e)}")
+
+        return alerts_to_create
+
+    def check_certificate_expiry(self, scan: Scan, rule: AlertRule) -> List[Dict[str, Any]]:
+        """
+        Check for certificates expiring within the threshold days.
+
+        Args:
+            scan: The scan to check
+            rule: The alert rule configuration
+
+        Returns:
+            List of alert data dictionaries
+        """
+        alerts_to_create = []
+        threshold_days = rule.threshold or 30  # Default 30 days
+
+        # Get all certificates from the scan
+        certificates = (
+            self.db.query(ScanCertificate, ScanPort, ScanIP)
+            .join(ScanServiceModel, ScanCertificate.service_id == ScanServiceModel.id)
+            .join(ScanPort, ScanServiceModel.port_id == ScanPort.id)
+            .join(ScanIP, ScanPort.ip_id == ScanIP.id)
+            .filter(ScanPort.scan_id == scan.id)
+            .all()
+        )
+
+        for cert, port, ip in certificates:
+            if cert.days_until_expiry is not None and cert.days_until_expiry <= threshold_days:
+                if cert.days_until_expiry <= 0:
+                    severity = 'critical'
+                    message = f"Certificate EXPIRED on {ip.ip_address}:{port.port}"
+                elif cert.days_until_expiry <= 7:
+                    severity = 'critical'
+                    message = f"Certificate expires in {cert.days_until_expiry} days on {ip.ip_address}:{port.port}"
+                elif cert.days_until_expiry <= 14:
+                    severity = 'warning'
+                    message = f"Certificate expires in {cert.days_until_expiry} days on {ip.ip_address}:{port.port}"
+                else:
+                    severity = 'info'
+                    message = f"Certificate expires in {cert.days_until_expiry} days on {ip.ip_address}:{port.port}"
+
+                alerts_to_create.append({
+                    'alert_type': 'cert_expiry',
+                    'severity': severity,
+                    'message': message,
+                    'ip_address': ip.ip_address,
+                    'port': port.port
+                })
+
+        return alerts_to_create
+
+    def check_weak_tls(self, scan: Scan, rule: AlertRule) -> List[Dict[str, Any]]:
+        """
+        Check for weak TLS versions (1.0, 1.1).
+
+        Args:
+            scan: The scan to check
+            rule: The alert rule configuration
+
+        Returns:
+            List of alert data dictionaries
+        """
+        alerts_to_create = []
+
+        # Get all TLS version data from the scan
+        tls_versions = (
+            self.db.query(ScanTLSVersion, ScanPort, ScanIP)
+            .join(ScanCertificate, ScanTLSVersion.certificate_id == ScanCertificate.id)
+            .join(ScanServiceModel, ScanCertificate.service_id == ScanServiceModel.id)
+            .join(ScanPort, ScanServiceModel.port_id == ScanPort.id)
+            .join(ScanIP, ScanPort.ip_id == ScanIP.id)
+            .filter(ScanPort.scan_id == scan.id)
+            .all()
+        )
+
+        # Group TLS versions by port/IP to create one alert per host
+        tls_by_host = {}
+        for tls, port, ip in tls_versions:
+            # Only alert on weak TLS versions that are supported
+            if tls.supported and tls.tls_version in ['TLS 1.0', 'TLS 1.1']:
+                key = (ip.ip_address, port.port)
+                if key not in tls_by_host:
+                    tls_by_host[key] = {'ip': ip.ip_address, 'port': port.port, 'versions': []}
+                tls_by_host[key]['versions'].append(tls.tls_version)
+
+        # Create alerts for hosts with weak TLS
+        for host_key, host_data in tls_by_host.items():
+            severity = rule.severity or 'warning'
+            alerts_to_create.append({
+                'alert_type': 'weak_tls',
+                'severity': severity,
+                'message': f"Weak TLS versions supported on {host_data['ip']}:{host_data['port']}: {', '.join(host_data['versions'])}",
+                'ip_address': host_data['ip'],
+                'port': host_data['port']
+            })
+
+        return alerts_to_create
+
+    def check_ping_failures(self, scan: Scan, rule: AlertRule) -> List[Dict[str, Any]]:
+        """
+        Check for hosts that were expected to respond to ping but didn't.
+
+        Args:
+            scan: The scan to check
+            rule: The alert rule configuration
+
+        Returns:
+            List of alert data dictionaries
+        """
+        alerts_to_create = []
+
+        # Get all IPs where ping was expected but failed
+        failed_pings = (
+            self.db.query(ScanIP)
+            .filter(ScanIP.scan_id == scan.id)
+            .filter(ScanIP.ping_expected == True)
+            .filter(ScanIP.ping_actual == False)
+            .all()
+        )
+
+        for ip in failed_pings:
+            severity = rule.severity or 'warning'
+            alerts_to_create.append({
+                'alert_type': 'ping_failed',
+                'severity': severity,
+                'message': f"Host {ip.ip_address} did not respond to ping (expected to be up)",
+                'ip_address': ip.ip_address,
+                'port': None
+            })
+
+        return alerts_to_create
+
+    def create_alert(self, scan_id: int, rule: AlertRule, alert_data: Dict[str, Any]) -> Optional[Alert]:
+        """
+        Create an alert record in the database.
+
+        Args:
+            scan_id: ID of the scan that triggered the alert
+            rule: The alert rule that was triggered
+            alert_data: Dictionary with alert details
+
+        Returns:
+            Created Alert object or None if creation failed
+        """
+        try:
+            alert = Alert(
+                scan_id=scan_id,
+                rule_id=rule.id,
+                alert_type=alert_data['alert_type'],
+                severity=alert_data['severity'],
+                message=alert_data['message'],
+                ip_address=alert_data.get('ip_address'),
+                port=alert_data.get('port'),
+                created_at=datetime.now(timezone.utc)
+            )
+
+            self.db.add(alert)
+            self.db.commit()
+
+            logger.info(f"Created alert: {alert.message}")
+            return alert
+
+        except Exception as e:
+            logger.error(f"Failed to create alert: {str(e)}")
+            self.db.rollback()
+            return None
+
+    def trigger_notifications(self, alert: Alert, rule: AlertRule):
+        """
+        Send notifications for an alert based on rule configuration.
+
+        Args:
+            alert: The alert to send notifications for
+            rule: The rule that specifies notification settings
+        """
+        # Email notification will be implemented in email_service.py
+        if rule.email_enabled:
+            logger.info(f"Email notification would be sent for alert {alert.id}")
+            # TODO: Call email service
+
+        # Webhook notification - queue for delivery
+        if rule.webhook_enabled:
+            try:
+                from flask import current_app
+                from .webhook_service import WebhookService
+
+                webhook_service = WebhookService(self.db)
+
+                # Get matching webhooks for this alert
+                matching_webhooks = webhook_service.get_matching_webhooks(alert)
+
+                if matching_webhooks:
+                    # Get scheduler from app context
+                    scheduler = getattr(current_app, 'scheduler', None)
+
+                    # Queue delivery for each matching webhook
+                    for webhook in matching_webhooks:
+                        webhook_service.queue_webhook_delivery(
+                            webhook.id,
+                            alert.id,
+                            scheduler_service=scheduler
+                        )
+                        logger.info(f"Queued webhook {webhook.id} ({webhook.name}) for alert {alert.id}")
+                else:
+                    logger.debug(f"No matching webhooks found for alert {alert.id}")
+
+            except Exception as e:
+                logger.error(f"Failed to queue webhook notifications for alert {alert.id}: {e}", exc_info=True)
+                # Don't fail alert creation if webhook queueing fails
+
+    def acknowledge_alert(self, alert_id: int, acknowledged_by: str = "system") -> bool:
+        """
+        Acknowledge an alert.
+
+        Args:
+            alert_id: ID of the alert to acknowledge
+            acknowledged_by: Username or system identifier
+
+        Returns:
+            True if successful, False otherwise
+        """
+        try:
+            alert = self.db.query(Alert).filter(Alert.id == alert_id).first()
+            if not alert:
+                logger.error(f"Alert {alert_id} not found")
+                return False
+
+            alert.acknowledged = True
+            alert.acknowledged_at = datetime.now(timezone.utc)
+            alert.acknowledged_by = acknowledged_by
+
+            self.db.commit()
+            logger.info(f"Alert {alert_id} acknowledged by {acknowledged_by}")
+            return True
+
+        except Exception as e:
+            logger.error(f"Failed to acknowledge alert {alert_id}: {str(e)}")
+            self.db.rollback()
+            return False
+
+    def get_alerts_for_scan(self, scan_id: int) -> List[Alert]:
+        """
+        Get all alerts for a specific scan.
+
+        Args:
+            scan_id: ID of the scan
+
+        Returns:
+            List of Alert objects
+        """
+        return (
+            self.db.query(Alert)
+            .filter(Alert.scan_id == scan_id)
+            .order_by(Alert.severity.desc(), Alert.created_at.desc())
+            .all()
+        )

app/web/services/config_service.py

@@ -0,0 +1,339 @@
+"""
+Config Service - Business logic for config management
+
+This service handles all operations related to scan configurations,
+both database-stored (primary) and file-based (deprecated).
+"""
+
+import os
+from typing import Dict, List, Any, Optional
+from datetime import datetime
+from sqlalchemy.orm import Session
+
+
+class ConfigService:
+    """Business logic for config management"""
+
+    def __init__(self, db_session: Session = None, configs_dir: str = '/app/configs'):
+        """
+        Initialize the config service.
+
+        Args:
+            db_session: SQLAlchemy database session (for database operations)
+            configs_dir: Directory where legacy config files are stored
+        """
+        self.db = db_session
+        self.configs_dir = configs_dir
+
+        # Ensure configs directory exists (for legacy YAML configs)
+        os.makedirs(self.configs_dir, exist_ok=True)
+
+    # ============================================================================
+    # Database-based Config Operations (Primary)
+    # ============================================================================
+
+    def create_config(self, title: str, description: Optional[str], site_ids: List[int]) -> Dict[str, Any]:
+        """
+        Create a new scan configuration in the database.
+
+        Args:
+            title: Configuration title
+            description: Optional configuration description
+            site_ids: List of site IDs to include in this config
+
+        Returns:
+            Created config as dictionary:
+            {
+                "id": 1,
+                "title": "Production Scan",
+                "description": "...",
+                "site_count": 3,
+                "sites": [...],
+                "created_at": "2025-11-19T10:30:00Z",
+                "updated_at": "2025-11-19T10:30:00Z"
+            }
+
+        Raises:
+            ValueError: If validation fails or sites don't exist
+        """
+        if not title or not title.strip():
+            raise ValueError("Title is required")
+
+        if not site_ids or len(site_ids) == 0:
+            raise ValueError("At least one site must be selected")
+
+        # Import models here to avoid circular imports
+        from web.models import ScanConfig, ScanConfigSite, Site
+
+        # Verify all sites exist
+        existing_sites = self.db.query(Site).filter(Site.id.in_(site_ids)).all()
+        if len(existing_sites) != len(site_ids):
+            found_ids = {s.id for s in existing_sites}
+            missing_ids = set(site_ids) - found_ids
+            raise ValueError(f"Sites not found: {missing_ids}")
+
+        # Create config
+        config = ScanConfig(
+            title=title.strip(),
+            description=description.strip() if description else None,
+            created_at=datetime.utcnow(),
+            updated_at=datetime.utcnow()
+        )
+
+        self.db.add(config)
+        self.db.flush()  # Get the config ID
+
+        # Create associations
+        for site_id in site_ids:
+            assoc = ScanConfigSite(
+                config_id=config.id,
+                site_id=site_id,
+                created_at=datetime.utcnow()
+            )
+            self.db.add(assoc)
+
+        self.db.commit()
+
+        return self.get_config_by_id(config.id)
+
+    def get_config_by_id(self, config_id: int) -> Dict[str, Any]:
+        """
+        Get a scan configuration by ID.
+
+        Args:
+            config_id: Configuration ID
+
+        Returns:
+            Config as dictionary with sites
+
+        Raises:
+            ValueError: If config not found
+        """
+        from web.models import ScanConfig
+
+        config = self.db.query(ScanConfig).filter_by(id=config_id).first()
+
+        if not config:
+            raise ValueError(f"Config with ID {config_id} not found")
+
+        # Get associated sites
+        sites = []
+        for assoc in config.site_associations:
+            site = assoc.site
+            sites.append({
+                'id': site.id,
+                'name': site.name,
+                'description': site.description,
+                'ip_count': len(site.ips)
+            })
+
+        return {
+            'id': config.id,
+            'title': config.title,
+            'description': config.description,
+            'site_count': len(sites),
+            'sites': sites,
+            'created_at': config.created_at.isoformat() + 'Z' if config.created_at else None,
+            'updated_at': config.updated_at.isoformat() + 'Z' if config.updated_at else None
+        }
+
+    def list_configs_db(self) -> List[Dict[str, Any]]:
+        """
+        List all scan configurations from database.
+
+        Returns:
+            List of config dictionaries with metadata
+        """
+        from web.models import ScanConfig
+
+        configs = self.db.query(ScanConfig).order_by(ScanConfig.updated_at.desc()).all()
+
+        result = []
+        for config in configs:
+            sites = []
+            for assoc in config.site_associations:
+                site = assoc.site
+                sites.append({
+                    'id': site.id,
+                    'name': site.name
+                })
+
+            result.append({
+                'id': config.id,
+                'title': config.title,
+                'description': config.description,
+                'site_count': len(sites),
+                'sites': sites,
+                'created_at': config.created_at.isoformat() + 'Z' if config.created_at else None,
+                'updated_at': config.updated_at.isoformat() + 'Z' if config.updated_at else None
+            })
+
+        return result
+
+    def update_config(self, config_id: int, title: Optional[str], description: Optional[str], site_ids: Optional[List[int]]) -> Dict[str, Any]:
+        """
+        Update a scan configuration.
+
+        Args:
+            config_id: Configuration ID to update
+            title: New title (optional)
+            description: New description (optional)
+            site_ids: New list of site IDs (optional, replaces existing)
+
+        Returns:
+            Updated config dictionary
+
+        Raises:
+            ValueError: If config not found or validation fails
+        """
+        from web.models import ScanConfig, ScanConfigSite, Site
+
+        config = self.db.query(ScanConfig).filter_by(id=config_id).first()
+
+        if not config:
+            raise ValueError(f"Config with ID {config_id} not found")
+
+        # Update fields if provided
+        if title is not None:
+            if not title.strip():
+                raise ValueError("Title cannot be empty")
+            config.title = title.strip()
+
+        if description is not None:
+            config.description = description.strip() if description.strip() else None
+
+        # Update sites if provided
+        if site_ids is not None:
+            if len(site_ids) == 0:
+                raise ValueError("At least one site must be selected")
+
+            # Verify all sites exist
+            existing_sites = self.db.query(Site).filter(Site.id.in_(site_ids)).all()
+            if len(existing_sites) != len(site_ids):
+                found_ids = {s.id for s in existing_sites}
+                missing_ids = set(site_ids) - found_ids
+                raise ValueError(f"Sites not found: {missing_ids}")
+
+            # Remove existing associations
+            self.db.query(ScanConfigSite).filter_by(config_id=config_id).delete()
+
+            # Create new associations
+            for site_id in site_ids:
+                assoc = ScanConfigSite(
+                    config_id=config_id,
+                    site_id=site_id,
+                    created_at=datetime.utcnow()
+                )
+                self.db.add(assoc)
+
+        config.updated_at = datetime.utcnow()
+        self.db.commit()
+
+        return self.get_config_by_id(config_id)
+
+    def delete_config(self, config_id: int) -> None:
+        """
+        Delete a scan configuration from database.
+
+        This will cascade delete associated ScanConfigSite records.
+        Schedules and scans referencing this config will have their
+        config_id set to NULL.
+
+        Args:
+            config_id: Configuration ID to delete
+
+        Raises:
+            ValueError: If config not found
+        """
+        from web.models import ScanConfig
+
+        config = self.db.query(ScanConfig).filter_by(id=config_id).first()
+
+        if not config:
+            raise ValueError(f"Config with ID {config_id} not found")
+
+        self.db.delete(config)
+        self.db.commit()
+
+    def add_site_to_config(self, config_id: int, site_id: int) -> Dict[str, Any]:
+        """
+        Add a site to an existing config.
+
+        Args:
+            config_id: Configuration ID
+            site_id: Site ID to add
+
+        Returns:
+            Updated config dictionary
+
+        Raises:
+            ValueError: If config or site not found, or association already exists
+        """
+        from web.models import ScanConfig, Site, ScanConfigSite
+
+        config = self.db.query(ScanConfig).filter_by(id=config_id).first()
+        if not config:
+            raise ValueError(f"Config with ID {config_id} not found")
+
+        site = self.db.query(Site).filter_by(id=site_id).first()
+        if not site:
+            raise ValueError(f"Site with ID {site_id} not found")
+
+        # Check if association already exists
+        existing = self.db.query(ScanConfigSite).filter_by(
+            config_id=config_id, site_id=site_id
+        ).first()
+
+        if existing:
+            raise ValueError(f"Site '{site.name}' is already in this config")
+
+        # Create association
+        assoc = ScanConfigSite(
+            config_id=config_id,
+            site_id=site_id,
+            created_at=datetime.utcnow()
+        )
+        self.db.add(assoc)
+
+        config.updated_at = datetime.utcnow()
+        self.db.commit()
+
+        return self.get_config_by_id(config_id)
+
+    def remove_site_from_config(self, config_id: int, site_id: int) -> Dict[str, Any]:
+        """
+        Remove a site from a config.
+
+        Args:
+            config_id: Configuration ID
+            site_id: Site ID to remove
+
+        Returns:
+            Updated config dictionary
+
+        Raises:
+            ValueError: If config not found, or removing would leave config empty
+        """
+        from web.models import ScanConfig, ScanConfigSite
+
+        config = self.db.query(ScanConfig).filter_by(id=config_id).first()
+        if not config:
+            raise ValueError(f"Config with ID {config_id} not found")
+
+        # Check if this would leave the config empty
+        current_site_count = len(config.site_associations)
+        if current_site_count <= 1:
+            raise ValueError("Cannot remove last site from config. Delete the config instead.")
+
+        # Remove association
+        deleted = self.db.query(ScanConfigSite).filter_by(
+            config_id=config_id, site_id=site_id
+        ).delete()
+
+        if deleted == 0:
+            raise ValueError(f"Site with ID {site_id} is not in this config")
+
+        config.updated_at = datetime.utcnow()
+        self.db.commit()
+
+        return self.get_config_by_id(config_id)

app/web/services/scan_service.py

@@ -16,10 +16,10 @@ from sqlalchemy.orm import Session, joinedload
 
 from web.models import (
     Scan, ScanSite, ScanIP, ScanPort, ScanService as ScanServiceModel,
-    ScanCertificate, ScanTLSVersion
+    ScanCertificate, ScanTLSVersion, Site, ScanSiteAssociation, SiteIP
 )
 from web.utils.pagination import paginate, PaginatedResult
-from web.utils.validators import validate_config_file, validate_scan_status
+from web.utils.validators import validate_scan_status
 
 logger = logging.getLogger(__name__)
 
@@ -41,8 +41,9 @@ class ScanService:
         """
         self.db = db_session
 
-    def trigger_scan(self, config_file: str, triggered_by: str = 'manual',
-                    schedule_id: Optional[int] = None, scheduler=None) -> int:
+    def trigger_scan(self, config_id: int,
+                    triggered_by: str = 'manual', schedule_id: Optional[int] = None,
+                    scheduler=None) -> int:
         """
         Trigger a new scan.
 
@@ -50,7 +51,7 @@ class ScanService:
         queues the scan for background execution.
 
         Args:
-            config_file: Path to YAML configuration file
+            config_id: Database config ID
             triggered_by: Source that triggered scan (manual, scheduled, api)
             schedule_id: Optional schedule ID if triggered by schedule
             scheduler: Optional SchedulerService instance for queuing background jobs
@@ -59,30 +60,21 @@ class ScanService:
             Scan ID of the created scan
 
         Raises:
-            ValueError: If config file is invalid
+            ValueError: If config is invalid
         """
-        # Validate config file
-        is_valid, error_msg = validate_config_file(config_file)
-        if not is_valid:
-            raise ValueError(f"Invalid config file: {error_msg}")
+        from web.models import ScanConfig
 
-        # Convert config_file to full path if it's just a filename
-        if not config_file.startswith('/'):
-            config_path = f'/app/configs/{config_file}'
-        else:
-            config_path = config_file
+        # Validate config exists
+        db_config = self.db.query(ScanConfig).filter_by(id=config_id).first()
+        if not db_config:
+            raise ValueError(f"Config with ID {config_id} not found")
 
-        # Load config to get title
-        import yaml
-        with open(config_path, 'r') as f:
-            config = yaml.safe_load(f)
-
-        # Create scan record
+        # Create scan record with config_id
         scan = Scan(
             timestamp=datetime.utcnow(),
             status='running',
-            config_file=config_file,
-            title=config.get('title', 'Untitled Scan'),
+            config_id=config_id,
+            title=db_config.title,
             triggered_by=triggered_by,
             schedule_id=schedule_id,
             created_at=datetime.utcnow()
@@ -92,12 +84,12 @@ class ScanService:
         self.db.commit()
         self.db.refresh(scan)
 
-        logger.info(f"Scan {scan.id} triggered via {triggered_by}")
+        logger.info(f"Scan {scan.id} triggered via {triggered_by} with config_id={config_id}")
 
         # Queue background job if scheduler provided
         if scheduler:
             try:
-                job_id = scheduler.queue_scan(scan.id, config_file)
+                job_id = scheduler.queue_scan(scan.id, config_id=config_id)
                 logger.info(f"Scan {scan.id} queued for background execution (job_id={job_id})")
             except Exception as e:
                 logger.error(f"Failed to queue scan {scan.id}: {str(e)}")
@@ -265,58 +257,128 @@ class ScanService:
         elif scan.status == 'failed':
             status_info['progress'] = 'Failed'
             status_info['error_message'] = scan.error_message
+        elif scan.status == 'cancelled':
+            status_info['progress'] = 'Cancelled'
+            status_info['error_message'] = scan.error_message
 
         return status_info
 
-    def cleanup_orphaned_scans(self) -> int:
+    def get_scans_by_ip(self, ip_address: str, limit: int = 10) -> List[Dict[str, Any]]:
         """
-        Clean up orphaned scans that are stuck in 'running' status.
+        Get the last N scans containing a specific IP address.
+
+        Args:
+            ip_address: IP address to search for
+            limit: Maximum number of scans to return (default: 10)
+
+        Returns:
+            List of scan summary dictionaries, most recent first
+        """
+        scans = (
+            self.db.query(Scan)
+            .join(ScanIP, Scan.id == ScanIP.scan_id)
+            .filter(ScanIP.ip_address == ip_address)
+            .filter(Scan.status == 'completed')
+            .order_by(Scan.timestamp.desc())
+            .limit(limit)
+            .all()
+        )
+
+        return [self._scan_to_summary_dict(scan) for scan in scans]
+
+    def cleanup_orphaned_scans(self) -> dict:
+        """
+        Clean up orphaned scans with smart recovery.
+
+        For scans stuck in 'running' or 'finalizing' status:
+        - If output files exist: mark as 'completed' (smart recovery)
+        - If no output files: mark as 'failed'
 
         This should be called on application startup to handle scans that
         were running when the system crashed or was restarted.
 
-        Scans in 'running' status are marked as 'failed' with an appropriate
-        error message indicating they were orphaned.
-
         Returns:
-            Number of orphaned scans cleaned up
+            Dictionary with cleanup results: {'recovered': N, 'failed': N, 'total': N}
         """
-        # Find all scans with status='running'
-        orphaned_scans = self.db.query(Scan).filter(Scan.status == 'running').all()
+        # Find all scans with status='running' or 'finalizing'
+        orphaned_scans = self.db.query(Scan).filter(
+            Scan.status.in_(['running', 'finalizing'])
+        ).all()
 
         if not orphaned_scans:
             logger.info("No orphaned scans found")
-            return 0
+            return {'recovered': 0, 'failed': 0, 'total': 0}
 
         count = len(orphaned_scans)
-        logger.warning(f"Found {count} orphaned scan(s) in 'running' status, marking as failed")
+        logger.warning(f"Found {count} orphaned scan(s), attempting smart recovery")
+
+        recovered_count = 0
+        failed_count = 0
+        output_dir = Path('/app/output')
 
-        # Mark each orphaned scan as failed
         for scan in orphaned_scans:
+            # Check for existing output files
+            output_exists = False
+            output_files_found = []
+
+            # Check paths stored in database
+            if scan.json_path and Path(scan.json_path).exists():
+                output_exists = True
+                output_files_found.append('json')
+            if scan.html_path and Path(scan.html_path).exists():
+                output_files_found.append('html')
+            if scan.zip_path and Path(scan.zip_path).exists():
+                output_files_found.append('zip')
+
+            # Also check by timestamp pattern if paths not stored yet
+            if not output_exists and scan.started_at and output_dir.exists():
+                timestamp_pattern = scan.started_at.strftime('%Y%m%d')
+                for json_file in output_dir.glob(f'scan_report_{timestamp_pattern}*.json'):
+                    output_exists = True
+                    output_files_found.append('json')
+                    # Update scan record with found paths
+                    scan.json_path = str(json_file)
+                    html_file = json_file.with_suffix('.html')
+                    if html_file.exists():
+                        scan.html_path = str(html_file)
+                        output_files_found.append('html')
+                    zip_file = json_file.with_suffix('.zip')
+                    if zip_file.exists():
+                        scan.zip_path = str(zip_file)
+                        output_files_found.append('zip')
+                    break
+
+            if output_exists:
+                # Smart recovery: outputs exist, mark as completed
+                scan.status = 'completed'
+                scan.error_message = f'Recovered from orphaned state (output files found: {", ".join(output_files_found)})'
+                recovered_count += 1
+                logger.info(f"Recovered orphaned scan {scan.id} as completed (files: {output_files_found})")
+            else:
+                # No outputs: mark as failed
                 scan.status = 'failed'
-            scan.completed_at = datetime.utcnow()
                 scan.error_message = (
                     "Scan was interrupted by system shutdown or crash. "
-                "The scan was running but did not complete normally."
+                    "No output files were generated."
                 )
+                failed_count += 1
+                logger.info(f"Marked orphaned scan {scan.id} as failed (no output files)")
 
-            # Calculate duration if we have a started_at time
+            scan.completed_at = datetime.utcnow()
             if scan.started_at:
-                duration = (datetime.utcnow() - scan.started_at).total_seconds()
-                scan.duration = duration
-
-            logger.info(
-                f"Marked orphaned scan {scan.id} as failed "
-                f"(started: {scan.started_at.isoformat() if scan.started_at else 'unknown'})"
-            )
+                scan.duration = (datetime.utcnow() - scan.started_at).total_seconds()
 
         self.db.commit()
-        logger.info(f"Cleaned up {count} orphaned scan(s)")
+        logger.info(f"Cleaned up {count} orphaned scan(s): {recovered_count} recovered, {failed_count} failed")
 
-        return count
+        return {
+            'recovered': recovered_count,
+            'failed': failed_count,
+            'total': count
+        }
 
     def _save_scan_to_db(self, report: Dict[str, Any], scan_id: int,
-                        status: str = 'completed') -> None:
+                        status: str = 'completed', output_paths: Dict = None) -> None:
         """
         Save scan results to database.
 
@@ -327,6 +389,7 @@ class ScanService:
             report: Scan report dictionary from scanner
             scan_id: Scan ID to update
             status: Final scan status (completed or failed)
+            output_paths: Dictionary with paths to generated files {'json': Path, 'html': Path, 'zip': Path}
         """
         scan = self.db.query(Scan).filter(Scan.id == scan_id).first()
         if not scan:
@@ -337,6 +400,17 @@ class ScanService:
         scan.duration = report.get('scan_duration')
         scan.completed_at = datetime.utcnow()
 
+        # Save output file paths
+        if output_paths:
+            if 'json' in output_paths:
+                scan.json_path = str(output_paths['json'])
+            if 'html' in output_paths:
+                scan.html_path = str(output_paths['html'])
+            if 'zip' in output_paths:
+                scan.zip_path = str(output_paths['zip'])
+            if 'screenshots' in output_paths:
+                scan.screenshot_dir = str(output_paths['screenshots'])
+
         # Map report data to database models
         self._map_report_to_models(report, scan)
 
@@ -366,6 +440,34 @@ class ScanService:
             self.db.add(site)
             self.db.flush()  # Get site.id for foreign key
 
+            # Create ScanSiteAssociation if this site exists in the database
+            # This links the scan to reusable site definitions
+            master_site = (
+                self.db.query(Site)
+                .filter(Site.name == site_data['name'])
+                .first()
+            )
+
+            if master_site:
+                # Check if association already exists (avoid duplicates)
+                existing_assoc = (
+                    self.db.query(ScanSiteAssociation)
+                    .filter(
+                        ScanSiteAssociation.scan_id == scan_obj.id,
+                        ScanSiteAssociation.site_id == master_site.id
+                    )
+                    .first()
+                )
+
+                if not existing_assoc:
+                    assoc = ScanSiteAssociation(
+                        scan_id=scan_obj.id,
+                        site_id=master_site.id,
+                        created_at=datetime.utcnow()
+                    )
+                    self.db.add(assoc)
+                    logger.debug(f"Created association between scan {scan_obj.id} and site '{master_site.name}' (id={master_site.id})")
+
             # Process each IP in this site
             for ip_data in site_data.get('ips', []):
                 # Create ScanIP record
@@ -419,9 +521,10 @@ class ScanService:
 
                         # Process certificate and TLS info if present
                         http_info = service_data.get('http_info', {})
-                        if http_info.get('certificate'):
+                        ssl_tls = http_info.get('ssl_tls', {})
+                        if ssl_tls.get('certificate'):
                             self._process_certificate(
-                                http_info['certificate'],
+                                ssl_tls,
                                 scan_obj.id,
                                 service.id
                             )
@@ -459,16 +562,19 @@ class ScanService:
                 return service
         return None
 
-    def _process_certificate(self, cert_data: Dict[str, Any], scan_id: int,
+    def _process_certificate(self, ssl_tls_data: Dict[str, Any], scan_id: int,
                             service_id: int) -> None:
         """
         Process certificate and TLS version data.
 
         Args:
-            cert_data: Certificate data dictionary
+            ssl_tls_data: SSL/TLS data dictionary containing 'certificate' and 'tls_versions'
             scan_id: Scan ID
             service_id: Service ID
         """
+        # Extract certificate data from ssl_tls structure
+        cert_data = ssl_tls_data.get('certificate', {})
+
         # Create ScanCertificate record
         cert = ScanCertificate(
             scan_id=scan_id,
@@ -486,7 +592,7 @@ class ScanService:
         self.db.flush()
 
         # Process TLS versions
-        tls_versions = cert_data.get('tls_versions', {})
+        tls_versions = ssl_tls_data.get('tls_versions', {})
         for version, version_data in tls_versions.items():
             tls = ScanTLSVersion(
                 scan_id=scan_id,
@@ -535,7 +641,7 @@ class ScanService:
             'duration': scan.duration,
             'status': scan.status,
             'title': scan.title,
-            'config_file': scan.config_file,
+            'config_id': scan.config_id,
             'json_path': scan.json_path,
             'html_path': scan.html_path,
             'zip_path': scan.zip_path,
@@ -561,23 +667,54 @@ class ScanService:
             'duration': scan.duration,
             'status': scan.status,
             'title': scan.title,
+            'config_id': scan.config_id,
             'triggered_by': scan.triggered_by,
             'created_at': scan.created_at.isoformat() if scan.created_at else None
         }
 
     def _site_to_dict(self, site: ScanSite) -> Dict[str, Any]:
         """Convert ScanSite to dictionary."""
+        # Look up the master Site ID from ScanSiteAssociation
+        master_site_id = None
+        assoc = (
+            self.db.query(ScanSiteAssociation)
+            .filter(
+                ScanSiteAssociation.scan_id == site.scan_id,
+            )
+            .join(Site)
+            .filter(Site.name == site.site_name)
+            .first()
+        )
+        if assoc:
+            master_site_id = assoc.site_id
+
         return {
             'id': site.id,
             'name': site.site_name,
-            'ips': [self._ip_to_dict(ip) for ip in site.ips]
+            'site_id': master_site_id,  # The actual Site ID for config updates
+            'ips': [self._ip_to_dict(ip, master_site_id) for ip in site.ips]
         }
 
-    def _ip_to_dict(self, ip: ScanIP) -> Dict[str, Any]:
+    def _ip_to_dict(self, ip: ScanIP, site_id: Optional[int] = None) -> Dict[str, Any]:
         """Convert ScanIP to dictionary."""
+        # Look up the SiteIP ID for this IP address in the master Site
+        site_ip_id = None
+        if site_id:
+            site_ip = (
+                self.db.query(SiteIP)
+                .filter(
+                    SiteIP.site_id == site_id,
+                    SiteIP.ip_address == ip.ip_address
+                )
+                .first()
+            )
+            if site_ip:
+                site_ip_id = site_ip.id
+
         return {
             'id': ip.id,
             'address': ip.ip_address,
+            'site_ip_id': site_ip_id,  # The actual SiteIP ID for config updates
             'ping_expected': ip.ping_expected,
             'ping_actual': ip.ping_actual,
             'ports': [self._port_to_dict(port) for port in ip.ports]
@@ -675,6 +812,8 @@ class ScanService:
             {
                 'scan1': {...},  # Scan 1 summary
                 'scan2': {...},  # Scan 2 summary
+                'same_config': bool,  # Whether both scans used the same config
+                'config_warning': str | None,  # Warning message if configs differ
                 'ports': {
                     'added': [...],
                     'removed': [...],
@@ -700,6 +839,22 @@ class ScanService:
         if not scan1 or not scan2:
             return None
 
+        # Check if scans use the same configuration
+        config1 = scan1.get('config_id')
+        config2 = scan2.get('config_id')
+        same_config = (config1 == config2) and (config1 is not None)
+
+        # Generate warning message if configs differ
+        config_warning = None
+        if not same_config:
+            config_warning = (
+                f"These scans use different configurations. "
+                f"Scan #{scan1_id} used config_id={config1 or 'unknown'} and "
+                f"Scan #{scan2_id} used config_id={config2 or 'unknown'}. "
+                f"The comparison may show all changes as additions/removals if the scans "
+                f"cover different IP ranges or infrastructure."
+            )
+
         # Extract port data
         ports1 = self._extract_ports_from_scan(scan1)
         ports2 = self._extract_ports_from_scan(scan2)
@@ -733,14 +888,18 @@ class ScanService:
                 'id': scan1['id'],
                 'timestamp': scan1['timestamp'],
                 'title': scan1['title'],
-                'status': scan1['status']
+                'status': scan1['status'],
+                'config_id': config1
             },
             'scan2': {
                 'id': scan2['id'],
                 'timestamp': scan2['timestamp'],
                 'title': scan2['title'],
-                'status': scan2['status']
+                'status': scan2['status'],
+                'config_id': config2
             },
+            'same_config': same_config,
+            'config_warning': config_warning,
             'ports': ports_comparison,
             'services': services_comparison,
             'certificates': certificates_comparison,

app/web/services/schedule_service.py

@@ -6,14 +6,13 @@ scheduled scans with cron expressions.
 """
 
 import logging
-import os
-from datetime import datetime
+from datetime import datetime, timezone
 from typing import Any, Dict, List, Optional, Tuple
 
 from croniter import croniter
 from sqlalchemy.orm import Session
 
-from web.models import Schedule, Scan
+from web.models import Schedule, Scan, ScanConfig
 from web.utils.pagination import paginate, PaginatedResult
 
 logger = logging.getLogger(__name__)
@@ -39,7 +38,7 @@ class ScheduleService:
     def create_schedule(
         self,
         name: str,
-        config_file: str,
+        config_id: int,
         cron_expression: str,
         enabled: bool = True
     ) -> int:
@@ -48,7 +47,7 @@ class ScheduleService:
 
         Args:
             name: Human-readable schedule name
-            config_file: Path to YAML configuration file
+            config_id: Database config ID
             cron_expression: Cron expression (e.g., '0 2 * * *')
             enabled: Whether schedule is active
 
@@ -56,36 +55,32 @@ class ScheduleService:
             Schedule ID of the created schedule
 
         Raises:
-            ValueError: If cron expression is invalid or config file doesn't exist
+            ValueError: If cron expression is invalid or config doesn't exist
         """
         # Validate cron expression
         is_valid, error_msg = self.validate_cron_expression(cron_expression)
         if not is_valid:
             raise ValueError(f"Invalid cron expression: {error_msg}")
 
-        # Validate config file exists
-        # If config_file is just a filename, prepend the configs directory
-        if not config_file.startswith('/'):
-            config_file_path = os.path.join('/app/configs', config_file)
-        else:
-            config_file_path = config_file
-
-        if not os.path.isfile(config_file_path):
-            raise ValueError(f"Config file not found: {config_file}")
+        # Validate config exists
+        db_config = self.db.query(ScanConfig).filter_by(id=config_id).first()
+        if not db_config:
+            raise ValueError(f"Config with ID {config_id} not found")
 
         # Calculate next run time
         next_run = self.calculate_next_run(cron_expression) if enabled else None
 
         # Create schedule record
+        now_utc = datetime.now(timezone.utc)
         schedule = Schedule(
             name=name,
-            config_file=config_file,
+            config_id=config_id,
             cron_expression=cron_expression,
             enabled=enabled,
             last_run=None,
             next_run=next_run,
-            created_at=datetime.utcnow(),
-            updated_at=datetime.utcnow()
+            created_at=now_utc,
+            updated_at=now_utc
         )
 
         self.db.add(schedule)
@@ -109,7 +104,14 @@ class ScheduleService:
         Raises:
             ValueError: If schedule not found
         """
-        schedule = self.db.query(Schedule).filter(Schedule.id == schedule_id).first()
+        from sqlalchemy.orm import joinedload
+
+        schedule = (
+            self.db.query(Schedule)
+            .options(joinedload(Schedule.config))
+            .filter(Schedule.id == schedule_id)
+            .first()
+        )
 
         if not schedule:
             raise ValueError(f"Schedule {schedule_id} not found")
@@ -144,8 +146,10 @@ class ScheduleService:
                 'pages': int
             }
         """
-        # Build query
-        query = self.db.query(Schedule)
+        from sqlalchemy.orm import joinedload
+
+        # Build query and eagerly load config relationship
+        query = self.db.query(Schedule).options(joinedload(Schedule.config))
 
         # Apply filter
         if enabled_filter is not None:
@@ -200,17 +204,11 @@ class ScheduleService:
             if schedule.enabled or updates.get('enabled', False):
                 updates['next_run'] = self.calculate_next_run(updates['cron_expression'])
 
-        # Validate config file if being updated
-        if 'config_file' in updates:
-            config_file = updates['config_file']
-            # If config_file is just a filename, prepend the configs directory
-            if not config_file.startswith('/'):
-                config_file_path = os.path.join('/app/configs', config_file)
-            else:
-                config_file_path = config_file
-
-            if not os.path.isfile(config_file_path):
-                raise ValueError(f"Config file not found: {updates['config_file']}")
+        # Validate config_id if being updated
+        if 'config_id' in updates:
+            db_config = self.db.query(ScanConfig).filter_by(id=updates['config_id']).first()
+            if not db_config:
+                raise ValueError(f"Config with ID {updates['config_id']} not found")
 
         # Handle enabled toggle
         if 'enabled' in updates:
@@ -227,7 +225,7 @@ class ScheduleService:
             if hasattr(schedule, key):
                 setattr(schedule, key, value)
 
-        schedule.updated_at = datetime.utcnow()
+        schedule.updated_at = datetime.now(timezone.utc)
 
         self.db.commit()
         self.db.refresh(schedule)
@@ -310,7 +308,7 @@ class ScheduleService:
 
         schedule.last_run = last_run
         schedule.next_run = next_run
-        schedule.updated_at = datetime.utcnow()
+        schedule.updated_at = datetime.now(timezone.utc)
 
         self.db.commit()
 
@@ -323,23 +321,43 @@ class ScheduleService:
         Validate a cron expression.
 
         Args:
-            cron_expr: Cron expression to validate
+            cron_expr: Cron expression to validate in standard crontab format
+                      Format: minute hour day month day_of_week
+                      Day of week: 0=Sunday, 1=Monday, ..., 6=Saturday
+                      (APScheduler will convert this to its internal format automatically)
 
         Returns:
             Tuple of (is_valid, error_message)
             - (True, None) if valid
             - (False, error_message) if invalid
+
+        Note:
+            This validates using croniter which uses standard crontab format.
+            APScheduler's from_crontab() will handle the conversion when the
+            schedule is registered with the scheduler.
         """
         try:
             # Try to create a croniter instance
-            base_time = datetime.utcnow()
+            # croniter uses standard crontab format (Sunday=0)
+            from datetime import timezone
+            base_time = datetime.now(timezone.utc)
             cron = croniter(cron_expr, base_time)
 
             # Try to get the next run time (validates the expression)
             cron.get_next(datetime)
 
+            # Validate basic format (5 fields)
+            fields = cron_expr.split()
+            if len(fields) != 5:
+                return (False, f"Cron expression must have 5 fields (minute hour day month day_of_week), got {len(fields)}")
+
             return (True, None)
         except (ValueError, KeyError) as e:
+            error_msg = str(e)
+            # Add helpful hint for day_of_week errors
+            if "day" in error_msg.lower() and len(cron_expr.split()) >= 5:
+                hint = "\nNote: Use standard crontab format where 0=Sunday, 1=Monday, ..., 6=Saturday"
+                return (False, f"{error_msg}{hint}")
             return (False, str(e))
         except Exception as e:
             return (False, f"Unexpected error: {str(e)}")
@@ -357,17 +375,24 @@ class ScheduleService:
             from_time: Base time (defaults to now UTC)
 
         Returns:
-            Next run datetime (UTC)
+            Next run datetime (UTC, timezone-aware)
 
         Raises:
             ValueError: If cron expression is invalid
         """
         if from_time is None:
-            from_time = datetime.utcnow()
+            from_time = datetime.now(timezone.utc)
 
         try:
             cron = croniter(cron_expr, from_time)
-            return cron.get_next(datetime)
+            next_run = cron.get_next(datetime)
+
+            # croniter returns naive datetime, so we need to add timezone info
+            # Since we're using UTC for all calculations, add UTC timezone
+            if next_run.tzinfo is None:
+                next_run = next_run.replace(tzinfo=timezone.utc)
+
+            return next_run
         except Exception as e:
             raise ValueError(f"Invalid cron expression '{cron_expr}': {str(e)}")
 
@@ -400,7 +425,7 @@ class ScheduleService:
                 'timestamp': scan.timestamp.isoformat() if scan.timestamp else None,
                 'status': scan.status,
                 'title': scan.title,
-                'config_file': scan.config_file
+                'config_id': scan.config_id
             }
             for scan in scans
         ]
@@ -415,10 +440,16 @@ class ScheduleService:
         Returns:
             Dictionary representation
         """
+        # Get config title if relationship is loaded
+        config_name = None
+        if schedule.config:
+            config_name = schedule.config.title
+
         return {
             'id': schedule.id,
             'name': schedule.name,
-            'config_file': schedule.config_file,
+            'config_id': schedule.config_id,
+            'config_name': config_name,
             'cron_expression': schedule.cron_expression,
             'enabled': schedule.enabled,
             'last_run': schedule.last_run.isoformat() if schedule.last_run else None,
@@ -433,7 +464,7 @@ class ScheduleService:
         Format datetime as relative time.
 
         Args:
-            dt: Datetime to format (UTC)
+            dt: Datetime to format (UTC, can be naive or aware)
 
         Returns:
             Human-readable relative time (e.g., "in 2 hours", "yesterday")
@@ -441,7 +472,13 @@ class ScheduleService:
         if dt is None:
             return None
 
-        now = datetime.utcnow()
+        # Ensure both datetimes are timezone-aware for comparison
+        now = datetime.now(timezone.utc)
+
+        # If dt is naive, assume it's UTC and add timezone info
+        if dt.tzinfo is None:
+            dt = dt.replace(tzinfo=timezone.utc)
+
         diff = dt - now
 
         # Future times

app/web/services/scheduler_service.py

@@ -131,7 +131,7 @@ class SchedulerService:
                     try:
                         self.add_scheduled_scan(
                             schedule_id=schedule.id,
-                            config_file=schedule.config_file,
+                            config_id=schedule.config_id,
                             cron_expression=schedule.cron_expression
                         )
                         logger.info(f"Loaded schedule {schedule.id}: '{schedule.name}'")
@@ -149,13 +149,58 @@ class SchedulerService:
         except Exception as e:
             logger.error(f"Error loading schedules on startup: {str(e)}", exc_info=True)
 
-    def queue_scan(self, scan_id: int, config_file: str) -> str:
+    @staticmethod
+    def validate_cron_expression(cron_expression: str) -> tuple[bool, str]:
+        """
+        Validate a cron expression and provide helpful feedback.
+
+        Args:
+            cron_expression: Cron expression to validate
+
+        Returns:
+            Tuple of (is_valid: bool, message: str)
+            - If valid: (True, "Valid cron expression")
+            - If invalid: (False, "Error message with details")
+
+        Note:
+            Standard crontab format: minute hour day month day_of_week
+            Day of week: 0=Sunday, 1=Monday, ..., 6=Saturday (or 7=Sunday)
+        """
+        from apscheduler.triggers.cron import CronTrigger
+
+        try:
+            # Try to parse the expression
+            trigger = CronTrigger.from_crontab(cron_expression)
+
+            # Validate basic format (5 fields)
+            fields = cron_expression.split()
+            if len(fields) != 5:
+                return False, f"Cron expression must have 5 fields (minute hour day month day_of_week), got {len(fields)}"
+
+            return True, "Valid cron expression"
+
+        except (ValueError, KeyError) as e:
+            error_msg = str(e)
+
+            # Provide helpful hints for common errors
+            if "day_of_week" in error_msg.lower() or (len(cron_expression.split()) >= 5):
+                # Check if day_of_week field might be using APScheduler format by mistake
+                fields = cron_expression.split()
+                if len(fields) == 5:
+                    dow_field = fields[4]
+                    if dow_field.isdigit() and int(dow_field) >= 0:
+                        hint = "\nNote: Use standard crontab format where 0=Sunday, 1=Monday, ..., 6=Saturday"
+                        return False, f"Invalid cron expression: {error_msg}{hint}"
+
+            return False, f"Invalid cron expression: {error_msg}"
+
+    def queue_scan(self, scan_id: int, config_id: int) -> str:
         """
         Queue a scan for immediate background execution.
 
         Args:
             scan_id: Database ID of the scan
-            config_file: Path to YAML configuration file
+            config_id: Database config ID
 
         Returns:
             Job ID from APScheduler
@@ -169,7 +214,7 @@ class SchedulerService:
         # Add job to run immediately
         job = self.scheduler.add_job(
             func=execute_scan,
-            args=[scan_id, config_file, self.db_url],
+            kwargs={'scan_id': scan_id, 'config_id': config_id, 'db_url': self.db_url},
             id=f'scan_{scan_id}',
             name=f'Scan {scan_id}',
             replace_existing=True,
@@ -179,15 +224,19 @@ class SchedulerService:
         logger.info(f"Queued scan {scan_id} for background execution (job_id={job.id})")
         return job.id
 
-    def add_scheduled_scan(self, schedule_id: int, config_file: str,
+    def add_scheduled_scan(self, schedule_id: int, config_id: int,
                           cron_expression: str) -> str:
         """
         Add a recurring scheduled scan.
 
         Args:
             schedule_id: Database ID of the schedule
-            config_file: Path to YAML configuration file
+            config_id: Database config ID
             cron_expression: Cron expression (e.g., "0 2 * * *" for 2am daily)
+                           IMPORTANT: Use standard crontab format where:
+                           - Day of week: 0 = Sunday, 1 = Monday, ..., 6 = Saturday
+                           - APScheduler automatically converts to its internal format
+                           - from_crontab() handles the conversion properly
 
         Returns:
             Job ID from APScheduler
@@ -195,18 +244,29 @@ class SchedulerService:
         Raises:
             RuntimeError: If scheduler not initialized
             ValueError: If cron expression is invalid
+
+        Note:
+            APScheduler internally uses Monday=0, but from_crontab() accepts
+            standard crontab format (Sunday=0) and converts it automatically.
         """
         if not self.scheduler:
             raise RuntimeError("Scheduler not initialized. Call init_scheduler() first.")
 
         from apscheduler.triggers.cron import CronTrigger
 
+        # Validate cron expression first to provide helpful error messages
+        is_valid, message = self.validate_cron_expression(cron_expression)
+        if not is_valid:
+            raise ValueError(message)
+
         # Create cron trigger from expression using local timezone
-        # This allows users to specify times in their local timezone
+        # from_crontab() parses standard crontab format (Sunday=0)
+        # and converts to APScheduler's internal format (Monday=0) automatically
         try:
             trigger = CronTrigger.from_crontab(cron_expression)
             # timezone defaults to local system timezone
         except (ValueError, KeyError) as e:
+            # This should not happen due to validation above, but catch anyway
             raise ValueError(f"Invalid cron expression '{cron_expression}': {str(e)}")
 
         # Add cron job
@@ -283,22 +343,27 @@ class SchedulerService:
                 # Create and trigger scan
                 scan_service = ScanService(session)
                 scan_id = scan_service.trigger_scan(
-                    config_file=schedule['config_file'],
+                    config_id=schedule['config_id'],
                     triggered_by='scheduled',
                     schedule_id=schedule_id,
                     scheduler=None  # Don't pass scheduler to avoid recursion
                 )
 
                 # Queue the scan for execution
-                self.queue_scan(scan_id, schedule['config_file'])
+                self.queue_scan(scan_id, schedule['config_id'])
 
                 # Update schedule's last_run and next_run
                 from croniter import croniter
-                next_run = croniter(schedule['cron_expression'], datetime.utcnow()).get_next(datetime)
+                now_utc = datetime.now(timezone.utc)
+                next_run = croniter(schedule['cron_expression'], now_utc).get_next(datetime)
+
+                # croniter returns naive datetime, add UTC timezone
+                if next_run.tzinfo is None:
+                    next_run = next_run.replace(tzinfo=timezone.utc)
 
                 schedule_service.update_run_times(
                     schedule_id=schedule_id,
-                    last_run=datetime.utcnow(),
+                    last_run=now_utc,
                     next_run=next_run
                 )
 

app/web/services/site_service.py

@@ -0,0 +1,683 @@
+"""
+Site service for managing reusable site definitions.
+
+This service handles the business logic for creating, updating, and managing
+sites with their associated CIDR ranges and IP-level overrides.
+"""
+
+import ipaddress
+import json
+import logging
+from datetime import datetime
+from typing import Any, Dict, List, Optional
+
+from sqlalchemy import func
+from sqlalchemy.orm import Session, joinedload
+
+from web.models import (
+    Site, SiteIP, ScanSiteAssociation
+)
+from web.utils.pagination import paginate, PaginatedResult
+
+logger = logging.getLogger(__name__)
+
+
+class SiteService:
+    """
+    Service for managing reusable site definitions.
+
+    Handles site lifecycle: creation, updates, deletion (with safety checks),
+    CIDR management, and IP-level overrides.
+    """
+
+    def __init__(self, db_session: Session):
+        """
+        Initialize site service.
+
+        Args:
+            db_session: SQLAlchemy database session
+        """
+        self.db = db_session
+
+    def create_site(self, name: str, description: Optional[str] = None) -> Dict[str, Any]:
+        """
+        Create a new site.
+
+        Args:
+            name: Unique site name
+            description: Optional site description
+
+        Returns:
+            Dictionary with created site data
+
+        Raises:
+            ValueError: If site name already exists
+        """
+        # Validate site name is unique
+        existing = self.db.query(Site).filter(Site.name == name).first()
+        if existing:
+            raise ValueError(f"Site with name '{name}' already exists")
+
+        # Create site (can be empty, IPs added separately)
+        site = Site(
+            name=name,
+            description=description,
+            created_at=datetime.utcnow(),
+            updated_at=datetime.utcnow()
+        )
+
+        self.db.add(site)
+        self.db.commit()
+        self.db.refresh(site)
+
+        logger.info(f"Created site '{name}' (id={site.id})")
+
+        return self._site_to_dict(site)
+
+    def update_site(self, site_id: int, name: Optional[str] = None,
+                   description: Optional[str] = None) -> Dict[str, Any]:
+        """
+        Update site metadata (name and/or description).
+
+        Args:
+            site_id: Site ID to update
+            name: New site name (must be unique)
+            description: New description
+
+        Returns:
+            Dictionary with updated site data
+
+        Raises:
+            ValueError: If site not found or name already exists
+        """
+        site = self.db.query(Site).filter(Site.id == site_id).first()
+        if not site:
+            raise ValueError(f"Site with id {site_id} not found")
+
+        # Update name if provided
+        if name is not None and name != site.name:
+            # Check uniqueness
+            existing = self.db.query(Site).filter(
+                Site.name == name,
+                Site.id != site_id
+            ).first()
+            if existing:
+                raise ValueError(f"Site with name '{name}' already exists")
+            site.name = name
+
+        # Update description if provided
+        if description is not None:
+            site.description = description
+
+        site.updated_at = datetime.utcnow()
+
+        self.db.commit()
+        self.db.refresh(site)
+
+        logger.info(f"Updated site {site_id} ('{site.name}')")
+
+        return self._site_to_dict(site)
+
+    def delete_site(self, site_id: int) -> None:
+        """
+        Delete a site.
+
+        Prevents deletion if the site is used in any scan (per user requirement).
+
+        Args:
+            site_id: Site ID to delete
+
+        Raises:
+            ValueError: If site not found or is used in scans
+        """
+        site = self.db.query(Site).filter(Site.id == site_id).first()
+        if not site:
+            raise ValueError(f"Site with id {site_id} not found")
+
+        # Check if site is used in any scans
+        usage_count = (
+            self.db.query(func.count(ScanSiteAssociation.id))
+            .filter(ScanSiteAssociation.site_id == site_id)
+            .scalar()
+        )
+
+        if usage_count > 0:
+            raise ValueError(
+                f"Cannot delete site '{site.name}': it is used in {usage_count} scan(s). "
+                f"Sites that have been used in scans cannot be deleted."
+            )
+
+        # Safe to delete
+        self.db.delete(site)
+        self.db.commit()
+
+        logger.info(f"Deleted site {site_id} ('{site.name}')")
+
+    def get_site(self, site_id: int) -> Optional[Dict[str, Any]]:
+        """
+        Get site details.
+
+        Args:
+            site_id: Site ID to retrieve
+
+        Returns:
+            Dictionary with site data, or None if not found
+        """
+        site = (
+            self.db.query(Site)
+            .filter(Site.id == site_id)
+            .first()
+        )
+
+        if not site:
+            return None
+
+        return self._site_to_dict(site)
+
+    def get_site_by_name(self, name: str) -> Optional[Dict[str, Any]]:
+        """
+        Get site details by name.
+
+        Args:
+            name: Site name to retrieve
+
+        Returns:
+            Dictionary with site data, or None if not found
+        """
+        site = (
+            self.db.query(Site)
+            .filter(Site.name == name)
+            .first()
+        )
+
+        if not site:
+            return None
+
+        return self._site_to_dict(site)
+
+    def list_sites(self, page: int = 1, per_page: int = 20) -> PaginatedResult:
+        """
+        List all sites with pagination.
+
+        Args:
+            page: Page number (1-indexed)
+            per_page: Number of items per page
+
+        Returns:
+            PaginatedResult with site data
+        """
+        query = (
+            self.db.query(Site)
+            .order_by(Site.name)
+        )
+
+        return paginate(query, page, per_page, self._site_to_dict)
+
+    def list_all_sites(self) -> List[Dict[str, Any]]:
+        """
+        List all sites without pagination (for dropdowns, etc.).
+
+        Returns:
+            List of site dictionaries
+        """
+        sites = (
+            self.db.query(Site)
+            .order_by(Site.name)
+            .all()
+        )
+
+        return [self._site_to_dict(site) for site in sites]
+
+    def get_global_ip_stats(self) -> Dict[str, int]:
+        """
+        Get global IP statistics across all sites.
+
+        Returns:
+            Dictionary with:
+                - total_ips: Total count of IP entries (including duplicates)
+                - unique_ips: Count of distinct IP addresses
+                - duplicate_ips: Number of duplicate entries (total - unique)
+        """
+        # Total IP entries
+        total_ips = (
+            self.db.query(func.count(SiteIP.id))
+            .scalar() or 0
+        )
+
+        # Unique IP addresses
+        unique_ips = (
+            self.db.query(func.count(func.distinct(SiteIP.ip_address)))
+            .scalar() or 0
+        )
+
+        return {
+            'total_ips': total_ips,
+            'unique_ips': unique_ips,
+            'duplicate_ips': total_ips - unique_ips
+        }
+
+    def bulk_add_ips_from_cidr(self, site_id: int, cidr: str,
+                              expected_ping: Optional[bool] = None,
+                              expected_tcp_ports: Optional[List[int]] = None,
+                              expected_udp_ports: Optional[List[int]] = None) -> Dict[str, Any]:
+        """
+        Expand a CIDR range and add all IPs to a site.
+
+        CIDRs are NOT stored - they are just used to generate IP records.
+
+        Args:
+            site_id: Site ID
+            cidr: CIDR notation (e.g., "10.0.0.0/24")
+            expected_ping: Expected ping response for all IPs
+            expected_tcp_ports: List of expected TCP ports for all IPs
+            expected_udp_ports: List of expected UDP ports for all IPs
+
+        Returns:
+            Dictionary with:
+                - cidr: The CIDR that was expanded
+                - ip_count: Number of IPs created
+                - ips_added: List of IP addresses created
+                - ips_skipped: List of IPs that already existed
+
+        Raises:
+            ValueError: If site not found or CIDR is invalid/too large
+        """
+        site = self.db.query(Site).filter(Site.id == site_id).first()
+        if not site:
+            raise ValueError(f"Site with id {site_id} not found")
+
+        # Validate CIDR format and size
+        try:
+            network = ipaddress.ip_network(cidr, strict=False)
+        except ValueError as e:
+            raise ValueError(f"Invalid CIDR notation '{cidr}': {str(e)}")
+
+        # Enforce CIDR size limits (max /24 for IPv4, /64 for IPv6)
+        if isinstance(network, ipaddress.IPv4Network) and network.prefixlen < 24:
+            raise ValueError(
+                f"CIDR '{cidr}' is too large ({network.num_addresses} IPs). "
+                f"Maximum allowed is /24 (256 IPs) for IPv4."
+            )
+        elif isinstance(network, ipaddress.IPv6Network) and network.prefixlen < 64:
+            raise ValueError(
+                f"CIDR '{cidr}' is too large. "
+                f"Maximum allowed is /64 for IPv6."
+            )
+
+        # Expand CIDR to individual IPs (no cidr_id since we're not storing CIDR)
+        ip_count, ips_added, ips_skipped = self._expand_cidr_to_ips(
+            site_id=site_id,
+            network=network,
+            expected_ping=expected_ping,
+            expected_tcp_ports=expected_tcp_ports or [],
+            expected_udp_ports=expected_udp_ports or []
+        )
+
+        site.updated_at = datetime.utcnow()
+        self.db.commit()
+
+        logger.info(
+            f"Expanded CIDR '{cidr}' for site {site_id} ('{site.name}'): "
+            f"added {ip_count} IPs, skipped {len(ips_skipped)} duplicates"
+        )
+
+        return {
+            'cidr': cidr,
+            'ip_count': ip_count,
+            'ips_added': ips_added,
+            'ips_skipped': ips_skipped
+        }
+
+    def bulk_add_ips_from_list(self, site_id: int, ip_list: List[str],
+                              expected_ping: Optional[bool] = None,
+                              expected_tcp_ports: Optional[List[int]] = None,
+                              expected_udp_ports: Optional[List[int]] = None) -> Dict[str, Any]:
+        """
+        Add multiple IPs from a list (e.g., from CSV/text import).
+
+        Args:
+            site_id: Site ID
+            ip_list: List of IP addresses as strings
+            expected_ping: Expected ping response for all IPs
+            expected_tcp_ports: List of expected TCP ports for all IPs
+            expected_udp_ports: List of expected UDP ports for all IPs
+
+        Returns:
+            Dictionary with:
+                - ip_count: Number of IPs successfully created
+                - ips_added: List of IP addresses created
+                - ips_skipped: List of IPs that already existed
+                - errors: List of validation errors {ip: error_message}
+
+        Raises:
+            ValueError: If site not found
+        """
+        site = self.db.query(Site).filter(Site.id == site_id).first()
+        if not site:
+            raise ValueError(f"Site with id {site_id} not found")
+
+        ips_added = []
+        ips_skipped = []
+        errors = []
+
+        for ip_str in ip_list:
+            ip_str = ip_str.strip()
+            if not ip_str:
+                continue  # Skip empty lines
+
+            # Validate IP format
+            try:
+                ipaddress.ip_address(ip_str)
+            except ValueError as e:
+                errors.append({'ip': ip_str, 'error': f"Invalid IP address: {str(e)}"})
+                continue
+
+            # Check for duplicate (across all IPs in the site)
+            existing = (
+                self.db.query(SiteIP)
+                .filter(SiteIP.site_id == site_id, SiteIP.ip_address == ip_str)
+                .first()
+            )
+            if existing:
+                ips_skipped.append(ip_str)
+                continue
+
+            # Create IP record
+            try:
+                ip_obj = SiteIP(
+                    site_id=site_id,
+                    ip_address=ip_str,
+                    expected_ping=expected_ping,
+                    expected_tcp_ports=json.dumps(expected_tcp_ports or []),
+                    expected_udp_ports=json.dumps(expected_udp_ports or []),
+                    created_at=datetime.utcnow()
+                )
+
+                self.db.add(ip_obj)
+                ips_added.append(ip_str)
+            except Exception as e:
+                errors.append({'ip': ip_str, 'error': f"Database error: {str(e)}"})
+
+        site.updated_at = datetime.utcnow()
+        self.db.commit()
+
+        logger.info(
+            f"Bulk added {len(ips_added)} IPs to site {site_id} ('{site.name}'), "
+            f"skipped {len(ips_skipped)} duplicates, {len(errors)} errors"
+        )
+
+        return {
+            'ip_count': len(ips_added),
+            'ips_added': ips_added,
+            'ips_skipped': ips_skipped,
+            'errors': errors
+        }
+
+    def add_standalone_ip(self, site_id: int, ip_address: str,
+                         expected_ping: Optional[bool] = None,
+                         expected_tcp_ports: Optional[List[int]] = None,
+                         expected_udp_ports: Optional[List[int]] = None) -> Dict[str, Any]:
+        """
+        Add a standalone IP (without a CIDR parent) to a site.
+
+        Args:
+            site_id: Site ID
+            ip_address: IP address to add
+            expected_ping: Expected ping response
+            expected_tcp_ports: List of expected TCP ports
+            expected_udp_ports: List of expected UDP ports
+
+        Returns:
+            Dictionary with IP data
+
+        Raises:
+            ValueError: If site not found, IP is invalid, or already exists
+        """
+        site = self.db.query(Site).filter(Site.id == site_id).first()
+        if not site:
+            raise ValueError(f"Site with id {site_id} not found")
+
+        # Validate IP format
+        try:
+            ipaddress.ip_address(ip_address)
+        except ValueError as e:
+            raise ValueError(f"Invalid IP address '{ip_address}': {str(e)}")
+
+        # Check for duplicate (across all IPs in the site)
+        existing = (
+            self.db.query(SiteIP)
+            .filter(SiteIP.site_id == site_id, SiteIP.ip_address == ip_address)
+            .first()
+        )
+        if existing:
+            raise ValueError(f"IP '{ip_address}' already exists in this site")
+
+        # Create IP
+        ip_obj = SiteIP(
+            site_id=site_id,
+            ip_address=ip_address,
+            expected_ping=expected_ping,
+            expected_tcp_ports=json.dumps(expected_tcp_ports or []),
+            expected_udp_ports=json.dumps(expected_udp_ports or []),
+            created_at=datetime.utcnow()
+        )
+
+        self.db.add(ip_obj)
+        site.updated_at = datetime.utcnow()
+        self.db.commit()
+        self.db.refresh(ip_obj)
+
+        logger.info(f"Added IP '{ip_address}' to site {site_id} ('{site.name}')")
+
+        return self._ip_to_dict(ip_obj)
+
+    def update_ip_settings(self, site_id: int, ip_id: int,
+                          expected_ping: Optional[bool] = None,
+                          expected_tcp_ports: Optional[List[int]] = None,
+                          expected_udp_ports: Optional[List[int]] = None) -> Dict[str, Any]:
+        """
+        Update settings for an individual IP.
+
+        Args:
+            site_id: Site ID
+            ip_id: IP ID to update
+            expected_ping: New ping expectation (if provided)
+            expected_tcp_ports: New TCP ports expectation (if provided)
+            expected_udp_ports: New UDP ports expectation (if provided)
+
+        Returns:
+            Dictionary with updated IP data
+
+        Raises:
+            ValueError: If IP not found
+        """
+        ip_obj = (
+            self.db.query(SiteIP)
+            .filter(SiteIP.id == ip_id, SiteIP.site_id == site_id)
+            .first()
+        )
+        if not ip_obj:
+            raise ValueError(f"IP with id {ip_id} not found for site {site_id}")
+
+        # Update settings if provided
+        if expected_ping is not None:
+            ip_obj.expected_ping = expected_ping
+        if expected_tcp_ports is not None:
+            ip_obj.expected_tcp_ports = json.dumps(expected_tcp_ports)
+        if expected_udp_ports is not None:
+            ip_obj.expected_udp_ports = json.dumps(expected_udp_ports)
+
+        self.db.commit()
+        self.db.refresh(ip_obj)
+
+        logger.info(f"Updated settings for IP '{ip_obj.ip_address}' in site {site_id}")
+
+        return self._ip_to_dict(ip_obj)
+
+    def remove_ip(self, site_id: int, ip_id: int) -> None:
+        """
+        Remove an IP from a site.
+
+        Args:
+            site_id: Site ID
+            ip_id: IP ID to remove
+
+        Raises:
+            ValueError: If IP not found
+        """
+        ip_obj = (
+            self.db.query(SiteIP)
+            .filter(SiteIP.id == ip_id, SiteIP.site_id == site_id)
+            .first()
+        )
+        if not ip_obj:
+            raise ValueError(f"IP with id {ip_id} not found for site {site_id}")
+
+        ip_address = ip_obj.ip_address
+        self.db.delete(ip_obj)
+        self.db.commit()
+
+        logger.info(f"Removed IP '{ip_address}' from site {site_id}")
+
+    def list_ips(self, site_id: int, page: int = 1, per_page: int = 50) -> PaginatedResult:
+        """
+        List IPs in a site with pagination.
+
+        Args:
+            site_id: Site ID
+            page: Page number (1-indexed)
+            per_page: Number of items per page
+
+        Returns:
+            PaginatedResult with IP data
+        """
+        query = (
+            self.db.query(SiteIP)
+            .filter(SiteIP.site_id == site_id)
+            .order_by(SiteIP.ip_address)
+        )
+
+        return paginate(query, page, per_page, self._ip_to_dict)
+
+    def get_scan_usage(self, site_id: int) -> List[Dict[str, Any]]:
+        """
+        Get list of scans that use this site.
+
+        Args:
+            site_id: Site ID
+
+        Returns:
+            List of scan dictionaries
+        """
+        from web.models import Scan  # Import here to avoid circular dependency
+
+        associations = (
+            self.db.query(ScanSiteAssociation)
+            .options(joinedload(ScanSiteAssociation.scan))
+            .filter(ScanSiteAssociation.site_id == site_id)
+            .all()
+        )
+
+        return [
+            {
+                'id': assoc.scan.id,
+                'title': assoc.scan.title,
+                'timestamp': assoc.scan.timestamp.isoformat() if assoc.scan.timestamp else None,
+                'status': assoc.scan.status
+            }
+            for assoc in associations
+        ]
+
+    # Private helper methods
+
+    def _expand_cidr_to_ips(self, site_id: int,
+                           network: ipaddress.IPv4Network | ipaddress.IPv6Network,
+                           expected_ping: Optional[bool],
+                           expected_tcp_ports: List[int],
+                           expected_udp_ports: List[int]) -> tuple[int, List[str], List[str]]:
+        """
+        Expand a CIDR to individual IP addresses.
+
+        Args:
+            site_id: Site ID
+            network: ipaddress network object
+            expected_ping: Default ping setting for all IPs
+            expected_tcp_ports: Default TCP ports for all IPs
+            expected_udp_ports: Default UDP ports for all IPs
+
+        Returns:
+            Tuple of (count of IPs created, list of IPs added, list of IPs skipped)
+        """
+        ip_count = 0
+        ips_added = []
+        ips_skipped = []
+
+        # For /32 or /128 (single host), use the network address
+        # For larger ranges, use hosts() to exclude network/broadcast addresses
+        if network.num_addresses == 1:
+            ip_list = [network.network_address]
+        elif network.num_addresses == 2:
+            # For /31 networks (point-to-point), both addresses are usable
+            ip_list = [network.network_address, network.broadcast_address]
+        else:
+            # Use hosts() to get usable IPs (excludes network and broadcast)
+            ip_list = list(network.hosts())
+
+        for ip in ip_list:
+            ip_str = str(ip)
+
+            # Check for duplicate
+            existing = (
+                self.db.query(SiteIP)
+                .filter(SiteIP.site_id == site_id, SiteIP.ip_address == ip_str)
+                .first()
+            )
+            if existing:
+                ips_skipped.append(ip_str)
+                continue
+
+            # Create SiteIP entry
+            ip_obj = SiteIP(
+                site_id=site_id,
+                ip_address=ip_str,
+                expected_ping=expected_ping,
+                expected_tcp_ports=json.dumps(expected_tcp_ports),
+                expected_udp_ports=json.dumps(expected_udp_ports),
+                created_at=datetime.utcnow()
+            )
+
+            self.db.add(ip_obj)
+            ips_added.append(ip_str)
+            ip_count += 1
+
+        return ip_count, ips_added, ips_skipped
+
+    def _site_to_dict(self, site: Site) -> Dict[str, Any]:
+        """Convert Site model to dictionary."""
+        # Count IPs for this site
+        ip_count = (
+            self.db.query(func.count(SiteIP.id))
+            .filter(SiteIP.site_id == site.id)
+            .scalar() or 0
+        )
+
+        return {
+            'id': site.id,
+            'name': site.name,
+            'description': site.description,
+            'created_at': site.created_at.isoformat() if site.created_at else None,
+            'updated_at': site.updated_at.isoformat() if site.updated_at else None,
+            'ip_count': ip_count
+        }
+
+    def _ip_to_dict(self, ip: SiteIP) -> Dict[str, Any]:
+        """Convert SiteIP model to dictionary."""
+        return {
+            'id': ip.id,
+            'site_id': ip.site_id,
+            'ip_address': ip.ip_address,
+            'expected_ping': ip.expected_ping,
+            'expected_tcp_ports': json.loads(ip.expected_tcp_ports) if ip.expected_tcp_ports else [],
+            'expected_udp_ports': json.loads(ip.expected_udp_ports) if ip.expected_udp_ports else [],
+            'created_at': ip.created_at.isoformat() if ip.created_at else None
+        }

app/web/services/template_service.py

@@ -0,0 +1,294 @@
+"""
+Webhook Template Service
+
+Provides Jinja2 template rendering for webhook payloads with a sandboxed
+environment and comprehensive context building from scan/alert/rule data.
+"""
+
+from jinja2 import Environment, BaseLoader, TemplateError, meta
+from jinja2.sandbox import SandboxedEnvironment
+import json
+from typing import Dict, Any, Optional, Tuple
+from datetime import datetime
+
+
+class TemplateService:
+    """
+    Service for rendering webhook templates safely using Jinja2.
+
+    Features:
+    - Sandboxed Jinja2 environment to prevent code execution
+    - Rich context with alert, scan, rule, service, cert data
+    - Support for both JSON and text output formats
+    - Template validation and error handling
+    """
+
+    def __init__(self):
+        """Initialize the sandboxed Jinja2 environment."""
+        self.env = SandboxedEnvironment(
+            loader=BaseLoader(),
+            autoescape=False,  # We control the output format
+            trim_blocks=True,
+            lstrip_blocks=True
+        )
+
+        # Add custom filters
+        self.env.filters['isoformat'] = self._isoformat_filter
+
+    def _isoformat_filter(self, value):
+        """Custom filter to convert datetime to ISO format."""
+        if isinstance(value, datetime):
+            return value.isoformat()
+        return str(value)
+
+    def build_context(
+        self,
+        alert,
+        scan,
+        rule,
+        app_name: str = "SneakyScanner",
+        app_version: str = "1.0.0",
+        app_url: str = "https://github.com/sneakygeek/SneakyScan"
+    ) -> Dict[str, Any]:
+        """
+        Build the template context from alert, scan, and rule objects.
+
+        Args:
+            alert: Alert model instance
+            scan: Scan model instance
+            rule: AlertRule model instance
+            app_name: Application name
+            app_version: Application version
+            app_url: Application repository URL
+
+        Returns:
+            Dictionary with all available template variables
+        """
+        context = {
+            "alert": {
+                "id": alert.id,
+                "type": alert.alert_type,
+                "severity": alert.severity,
+                "message": alert.message,
+                "ip_address": alert.ip_address,
+                "port": alert.port,
+                "acknowledged": alert.acknowledged,
+                "acknowledged_at": alert.acknowledged_at,
+                "acknowledged_by": alert.acknowledged_by,
+                "created_at": alert.created_at,
+                "email_sent": alert.email_sent,
+                "email_sent_at": alert.email_sent_at,
+                "webhook_sent": alert.webhook_sent,
+                "webhook_sent_at": alert.webhook_sent_at,
+            },
+            "scan": {
+                "id": scan.id,
+                "title": scan.title,
+                "timestamp": scan.timestamp,
+                "duration": scan.duration,
+                "status": scan.status,
+                "config_id": scan.config_id,
+                "triggered_by": scan.triggered_by,
+                "started_at": scan.started_at,
+                "completed_at": scan.completed_at,
+                "error_message": scan.error_message,
+            },
+            "rule": {
+                "id": rule.id,
+                "name": rule.name,
+                "type": rule.rule_type,
+                "threshold": rule.threshold,
+                "severity": rule.severity,
+                "enabled": rule.enabled,
+            },
+            "app": {
+                "name": app_name,
+                "version": app_version,
+                "url": app_url,
+            },
+            "timestamp": datetime.utcnow(),
+        }
+
+        # Add service information if available (for service-related alerts)
+        # This would require additional context from the caller
+        # For now, we'll add placeholder support
+        context["service"] = None
+        context["cert"] = None
+        context["tls"] = None
+
+        return context
+
+    def render(
+        self,
+        template_string: str,
+        context: Dict[str, Any],
+        template_format: str = 'json'
+    ) -> Tuple[str, Optional[str]]:
+        """
+        Render a template with the given context.
+
+        Args:
+            template_string: The Jinja2 template string
+            context: Template context dictionary
+            template_format: Output format ('json' or 'text')
+
+        Returns:
+            Tuple of (rendered_output, error_message)
+            - If successful: (rendered_string, None)
+            - If failed: (None, error_message)
+        """
+        try:
+            template = self.env.from_string(template_string)
+            rendered = template.render(context)
+
+            # For JSON format, validate that the output is valid JSON
+            if template_format == 'json':
+                try:
+                    # Parse to validate JSON structure
+                    json.loads(rendered)
+                except json.JSONDecodeError as e:
+                    return None, f"Template rendered invalid JSON: {str(e)}"
+
+            return rendered, None
+
+        except TemplateError as e:
+            return None, f"Template rendering error: {str(e)}"
+        except Exception as e:
+            return None, f"Unexpected error rendering template: {str(e)}"
+
+    def validate_template(
+        self,
+        template_string: str,
+        template_format: str = 'json'
+    ) -> Tuple[bool, Optional[str]]:
+        """
+        Validate a template without rendering it.
+
+        Args:
+            template_string: The Jinja2 template string to validate
+            template_format: Expected output format ('json' or 'text')
+
+        Returns:
+            Tuple of (is_valid, error_message)
+            - If valid: (True, None)
+            - If invalid: (False, error_message)
+        """
+        try:
+            # Parse the template to check syntax
+            self.env.parse(template_string)
+
+            # For JSON templates, check if it looks like valid JSON structure
+            # (this is a basic check - full validation happens during render)
+            if template_format == 'json':
+                # Just check for basic JSON structure markers
+                stripped = template_string.strip()
+                if not (stripped.startswith('{') or stripped.startswith('[')):
+                    return False, "JSON template must start with { or ["
+
+            return True, None
+
+        except TemplateError as e:
+            return False, f"Template syntax error: {str(e)}"
+        except Exception as e:
+            return False, f"Template validation error: {str(e)}"
+
+    def get_template_variables(self, template_string: str) -> set:
+        """
+        Extract all variables used in a template.
+
+        Args:
+            template_string: The Jinja2 template string
+
+        Returns:
+            Set of variable names used in the template
+        """
+        try:
+            ast = self.env.parse(template_string)
+            return meta.find_undeclared_variables(ast)
+        except Exception:
+            return set()
+
+    def render_test_payload(
+        self,
+        template_string: str,
+        template_format: str = 'json'
+    ) -> Tuple[str, Optional[str]]:
+        """
+        Render a template with sample/test data for preview purposes.
+
+        Args:
+            template_string: The Jinja2 template string
+            template_format: Output format ('json' or 'text')
+
+        Returns:
+            Tuple of (rendered_output, error_message)
+        """
+        # Create sample context data
+        sample_context = {
+            "alert": {
+                "id": 123,
+                "type": "unexpected_port",
+                "severity": "warning",
+                "message": "Unexpected port 8080 found open on 192.168.1.100",
+                "ip_address": "192.168.1.100",
+                "port": 8080,
+                "acknowledged": False,
+                "acknowledged_at": None,
+                "acknowledged_by": None,
+                "created_at": datetime.utcnow(),
+                "email_sent": False,
+                "email_sent_at": None,
+                "webhook_sent": False,
+                "webhook_sent_at": None,
+            },
+            "scan": {
+                "id": 456,
+                "title": "Production Infrastructure Scan",
+                "timestamp": datetime.utcnow(),
+                "duration": 125.5,
+                "status": "completed",
+                "config_id": 1,
+                "triggered_by": "schedule",
+                "started_at": datetime.utcnow(),
+                "completed_at": datetime.utcnow(),
+                "error_message": None,
+            },
+            "rule": {
+                "id": 789,
+                "name": "Unexpected Port Detection",
+                "type": "unexpected_port",
+                "threshold": None,
+                "severity": "warning",
+                "enabled": True,
+            },
+            "service": {
+                "name": "http",
+                "product": "nginx",
+                "version": "1.20.0",
+            },
+            "cert": {
+                "subject": "CN=example.com",
+                "issuer": "CN=Let's Encrypt Authority X3",
+                "days_until_expiry": 15,
+            },
+            "app": {
+                "name": "SneakyScanner",
+                "version": "1.0.0-phase5",
+                "url": "https://github.com/sneakygeek/SneakyScan",
+            },
+            "timestamp": datetime.utcnow(),
+        }
+
+        return self.render(template_string, sample_context, template_format)
+
+
+# Singleton instance
+_template_service = None
+
+
+def get_template_service() -> TemplateService:
+    """Get the singleton TemplateService instance."""
+    global _template_service
+    if _template_service is None:
+        _template_service = TemplateService()
+    return _template_service

app/web/services/webhook_service.py

@@ -0,0 +1,566 @@
+"""
+Webhook Service Module
+
+Handles webhook delivery for alert notifications with retry logic,
+authentication support, and comprehensive logging.
+"""
+
+import json
+import logging
+import time
+from datetime import datetime, timezone
+from typing import List, Dict, Optional, Any, Tuple
+from sqlalchemy.orm import Session
+import requests
+from requests.auth import HTTPBasicAuth
+
+from cryptography.fernet import Fernet
+import os
+
+from ..models import Webhook, WebhookDeliveryLog, Alert, AlertRule, Scan
+from .template_service import get_template_service
+from ..config import APP_NAME, APP_VERSION, REPO_URL
+
+logger = logging.getLogger(__name__)
+
+
+class WebhookService:
+    """
+    Service for webhook delivery and management.
+
+    Handles queuing webhook deliveries, executing HTTP requests with
+    authentication, retry logic, and logging delivery attempts.
+    """
+
+    def __init__(self, db_session: Session, encryption_key: Optional[bytes] = None):
+        """
+        Initialize webhook service.
+
+        Args:
+            db_session: SQLAlchemy database session
+            encryption_key: Fernet encryption key for auth_token encryption
+        """
+        self.db = db_session
+        self._encryption_key = encryption_key or self._get_encryption_key()
+        self._cipher = Fernet(self._encryption_key) if self._encryption_key else None
+
+    def _get_encryption_key(self) -> Optional[bytes]:
+        """
+        Get encryption key from environment or database.
+
+        Returns:
+            Fernet encryption key or None if not available
+        """
+        # Try environment variable first
+        key_str = os.environ.get('SNEAKYSCANNER_ENCRYPTION_KEY')
+        if key_str:
+            return key_str.encode()
+
+        # Try to get from settings (would need to query Setting table)
+        # For now, generate a temporary key if none exists
+        try:
+            return Fernet.generate_key()
+        except Exception as e:
+            logger.warning(f"Could not generate encryption key: {e}")
+            return None
+
+    def _encrypt_value(self, value: str) -> str:
+        """Encrypt a string value."""
+        if not self._cipher:
+            return value  # Return plain text if encryption not available
+        return self._cipher.encrypt(value.encode()).decode()
+
+    def _decrypt_value(self, encrypted_value: str) -> str:
+        """Decrypt an encrypted string value."""
+        if not self._cipher:
+            return encrypted_value  # Return as-is if encryption not available
+        try:
+            return self._cipher.decrypt(encrypted_value.encode()).decode()
+        except Exception as e:
+            logger.error(f"Failed to decrypt value: {e}")
+            return encrypted_value
+
+    def get_matching_webhooks(self, alert: Alert) -> List[Webhook]:
+        """
+        Get all enabled webhooks that match an alert's type and severity.
+
+        Args:
+            alert: Alert object to match against
+
+        Returns:
+            List of matching Webhook objects
+        """
+        # Get all enabled webhooks
+        webhooks = self.db.query(Webhook).filter(Webhook.enabled == True).all()
+
+        matching_webhooks = []
+        for webhook in webhooks:
+            # Check if webhook matches alert type filter
+            if webhook.alert_types:
+                try:
+                    alert_types = json.loads(webhook.alert_types)
+                    if alert.alert_type not in alert_types:
+                        continue  # Skip if alert type doesn't match
+                except json.JSONDecodeError:
+                    logger.warning(f"Invalid alert_types JSON for webhook {webhook.id}")
+                    continue
+
+            # Check if webhook matches severity filter
+            if webhook.severity_filter:
+                try:
+                    severity_filter = json.loads(webhook.severity_filter)
+                    if alert.severity not in severity_filter:
+                        continue  # Skip if severity doesn't match
+                except json.JSONDecodeError:
+                    logger.warning(f"Invalid severity_filter JSON for webhook {webhook.id}")
+                    continue
+
+            matching_webhooks.append(webhook)
+
+        logger.info(f"Found {len(matching_webhooks)} matching webhooks for alert {alert.id}")
+        return matching_webhooks
+
+    def queue_webhook_delivery(self, webhook_id: int, alert_id: int, scheduler_service=None) -> bool:
+        """
+        Queue a webhook delivery for async execution via APScheduler.
+
+        Args:
+            webhook_id: ID of webhook to deliver
+            alert_id: ID of alert to send
+            scheduler_service: SchedulerService instance (if None, deliver synchronously)
+
+        Returns:
+            True if queued successfully, False otherwise
+        """
+        if scheduler_service and scheduler_service.scheduler:
+            try:
+                # Import here to avoid circular dependency
+                from web.jobs.webhook_job import execute_webhook_delivery
+
+                # Schedule immediate execution
+                scheduler_service.scheduler.add_job(
+                    execute_webhook_delivery,
+                    args=[webhook_id, alert_id, scheduler_service.db_url],
+                    id=f"webhook_{webhook_id}_{alert_id}_{int(time.time())}",
+                    replace_existing=False
+                )
+                logger.info(f"Queued webhook {webhook_id} for alert {alert_id}")
+                return True
+            except Exception as e:
+                logger.error(f"Failed to queue webhook delivery: {e}")
+                # Fall back to synchronous delivery
+                return self.deliver_webhook(webhook_id, alert_id)
+        else:
+            # No scheduler available, deliver synchronously
+            logger.info(f"No scheduler available, delivering webhook {webhook_id} synchronously")
+            return self.deliver_webhook(webhook_id, alert_id)
+
+    def deliver_webhook(self, webhook_id: int, alert_id: int, attempt_number: int = 1) -> bool:
+        """
+        Deliver a webhook with retry logic.
+
+        Args:
+            webhook_id: ID of webhook to deliver
+            alert_id: ID of alert to send
+            attempt_number: Current attempt number (for retries)
+
+        Returns:
+            True if delivered successfully, False otherwise
+        """
+        # Get webhook and alert
+        webhook = self.db.query(Webhook).filter(Webhook.id == webhook_id).first()
+        if not webhook:
+            logger.error(f"Webhook {webhook_id} not found")
+            return False
+
+        alert = self.db.query(Alert).filter(Alert.id == alert_id).first()
+        if not alert:
+            logger.error(f"Alert {alert_id} not found")
+            return False
+
+        logger.info(f"Delivering webhook {webhook_id} for alert {alert_id} (attempt {attempt_number}/{webhook.retry_count})")
+
+        # Build payload with template support
+        payload, content_type = self._build_payload(webhook, alert)
+
+        # Prepare headers
+        headers = {'Content-Type': content_type}
+
+        # Add custom headers if provided
+        if webhook.custom_headers:
+            try:
+                custom_headers = json.loads(webhook.custom_headers)
+                headers.update(custom_headers)
+            except json.JSONDecodeError:
+                logger.warning(f"Invalid custom_headers JSON for webhook {webhook_id}")
+
+        # Prepare authentication
+        auth = None
+        if webhook.auth_type == 'bearer' and webhook.auth_token:
+            decrypted_token = self._decrypt_value(webhook.auth_token)
+            headers['Authorization'] = f'Bearer {decrypted_token}'
+        elif webhook.auth_type == 'basic' and webhook.auth_token:
+            # Expecting format: "username:password"
+            decrypted_token = self._decrypt_value(webhook.auth_token)
+            if ':' in decrypted_token:
+                username, password = decrypted_token.split(':', 1)
+                auth = HTTPBasicAuth(username, password)
+
+        # Execute HTTP request
+        try:
+            timeout = webhook.timeout or 10
+
+            # Use appropriate parameter based on payload type
+            if isinstance(payload, dict):
+                # JSON payload
+                response = requests.post(
+                    webhook.url,
+                    json=payload,
+                    headers=headers,
+                    auth=auth,
+                    timeout=timeout
+                )
+            else:
+                # Text payload
+                response = requests.post(
+                    webhook.url,
+                    data=payload,
+                    headers=headers,
+                    auth=auth,
+                    timeout=timeout
+                )
+
+            # Log delivery attempt
+            log_entry = WebhookDeliveryLog(
+                webhook_id=webhook_id,
+                alert_id=alert_id,
+                status='success' if response.status_code < 400 else 'failed',
+                response_code=response.status_code,
+                response_body=response.text[:1000],  # Limit to 1000 chars
+                error_message=None if response.status_code < 400 else f"HTTP {response.status_code}",
+                attempt_number=attempt_number,
+                delivered_at=datetime.now(timezone.utc)
+            )
+            self.db.add(log_entry)
+
+            # Update alert webhook status if successful
+            if response.status_code < 400:
+                alert.webhook_sent = True
+                alert.webhook_sent_at = datetime.now(timezone.utc)
+                logger.info(f"Webhook {webhook_id} delivered successfully (HTTP {response.status_code})")
+                self.db.commit()
+                return True
+            else:
+                # Failed but got a response
+                logger.warning(f"Webhook {webhook_id} failed with HTTP {response.status_code}")
+                self.db.commit()
+
+                # Retry if attempts remaining
+                if attempt_number < webhook.retry_count:
+                    delay = self._calculate_retry_delay(attempt_number)
+                    logger.info(f"Retrying webhook {webhook_id} in {delay} seconds")
+                    time.sleep(delay)
+                    return self.deliver_webhook(webhook_id, alert_id, attempt_number + 1)
+                return False
+
+        except requests.exceptions.Timeout:
+            error_msg = f"Request timeout after {timeout} seconds"
+            logger.error(f"Webhook {webhook_id} timeout: {error_msg}")
+            self._log_delivery_failure(webhook_id, alert_id, error_msg, attempt_number)
+
+        except requests.exceptions.ConnectionError as e:
+            error_msg = f"Connection error: {str(e)}"
+            logger.error(f"Webhook {webhook_id} connection error: {error_msg}")
+            self._log_delivery_failure(webhook_id, alert_id, error_msg, attempt_number)
+
+        except requests.exceptions.RequestException as e:
+            error_msg = f"Request error: {str(e)}"
+            logger.error(f"Webhook {webhook_id} request error: {error_msg}")
+            self._log_delivery_failure(webhook_id, alert_id, error_msg, attempt_number)
+
+        except Exception as e:
+            error_msg = f"Unexpected error: {str(e)}"
+            logger.error(f"Webhook {webhook_id} unexpected error: {error_msg}")
+            self._log_delivery_failure(webhook_id, alert_id, error_msg, attempt_number)
+
+        # Retry if attempts remaining
+        if attempt_number < webhook.retry_count:
+            delay = self._calculate_retry_delay(attempt_number)
+            logger.info(f"Retrying webhook {webhook_id} in {delay} seconds")
+            time.sleep(delay)
+            return self.deliver_webhook(webhook_id, alert_id, attempt_number + 1)
+
+        return False
+
+    def _log_delivery_failure(self, webhook_id: int, alert_id: int, error_message: str, attempt_number: int):
+        """Log a failed delivery attempt."""
+        log_entry = WebhookDeliveryLog(
+            webhook_id=webhook_id,
+            alert_id=alert_id,
+            status='failed',
+            response_code=None,
+            response_body=None,
+            error_message=error_message[:500],  # Limit error message length
+            attempt_number=attempt_number,
+            delivered_at=datetime.now(timezone.utc)
+        )
+        self.db.add(log_entry)
+        self.db.commit()
+
+    def _calculate_retry_delay(self, attempt_number: int) -> int:
+        """
+        Calculate exponential backoff delay for retries.
+
+        Args:
+            attempt_number: Current attempt number
+
+        Returns:
+            Delay in seconds
+        """
+        # Exponential backoff: 2^attempt seconds (2, 4, 8, 16...)
+        return min(2 ** attempt_number, 60)  # Cap at 60 seconds
+
+    def _build_payload(self, webhook: Webhook, alert: Alert) -> Tuple[Any, str]:
+        """
+        Build payload for webhook delivery using template if configured.
+
+        Args:
+            webhook: Webhook object with optional template configuration
+            alert: Alert object
+
+        Returns:
+            Tuple of (payload, content_type):
+            - payload: Rendered payload (dict for JSON, string for text)
+            - content_type: Content-Type header value
+        """
+        # Get related scan
+        scan = self.db.query(Scan).filter(Scan.id == alert.scan_id).first()
+
+        # Get related rule
+        rule = self.db.query(AlertRule).filter(AlertRule.id == alert.rule_id).first()
+
+        # If webhook has a custom template, use it
+        if webhook.template:
+            template_service = get_template_service()
+            context = template_service.build_context(
+                alert=alert,
+                scan=scan,
+                rule=rule,
+                app_name=APP_NAME,
+                app_version=APP_VERSION,
+                app_url=REPO_URL
+            )
+
+            rendered, error = template_service.render(
+                webhook.template,
+                context,
+                webhook.template_format or 'json'
+            )
+
+            if error:
+                logger.error(f"Template rendering error for webhook {webhook.id}: {error}")
+                # Fall back to default payload
+                return self._build_default_payload(alert, scan, rule), 'application/json'
+
+            # Determine content type
+            if webhook.content_type_override:
+                content_type = webhook.content_type_override
+            elif webhook.template_format == 'text':
+                content_type = 'text/plain'
+            else:
+                content_type = 'application/json'
+
+            # For JSON format, parse the rendered string back to a dict
+            # For text format, return as string
+            if webhook.template_format == 'json':
+                try:
+                    payload = json.loads(rendered)
+                except json.JSONDecodeError:
+                    logger.error(f"Failed to parse rendered JSON template for webhook {webhook.id}")
+                    return self._build_default_payload(alert, scan, rule), 'application/json'
+            else:
+                payload = rendered
+
+            return payload, content_type
+
+        # No template - use default payload
+        return self._build_default_payload(alert, scan, rule), 'application/json'
+
+    def _build_default_payload(self, alert: Alert, scan: Optional[Scan], rule: Optional[AlertRule]) -> Dict[str, Any]:
+        """
+        Build default JSON payload for webhook delivery.
+
+        Args:
+            alert: Alert object
+            scan: Scan object (optional)
+            rule: AlertRule object (optional)
+
+        Returns:
+            Dict containing alert details in generic JSON format
+        """
+        payload = {
+            "event": "alert.created",
+            "alert": {
+                "id": alert.id,
+                "type": alert.alert_type,
+                "severity": alert.severity,
+                "message": alert.message,
+                "ip_address": alert.ip_address,
+                "port": alert.port,
+                "acknowledged": alert.acknowledged,
+                "created_at": alert.created_at.isoformat() if alert.created_at else None
+            },
+            "scan": {
+                "id": scan.id if scan else None,
+                "title": scan.title if scan else None,
+                "timestamp": scan.timestamp.isoformat() if scan and scan.timestamp else None,
+                "status": scan.status if scan else None
+            },
+            "rule": {
+                "id": rule.id if rule else None,
+                "name": rule.name if rule else None,
+                "type": rule.rule_type if rule else None,
+                "threshold": rule.threshold if rule else None
+            }
+        }
+
+        return payload
+
+    def test_webhook(self, webhook_id: int) -> Dict[str, Any]:
+        """
+        Send a test payload to a webhook.
+
+        Args:
+            webhook_id: ID of webhook to test
+
+        Returns:
+            Dict with test result details
+        """
+        webhook = self.db.query(Webhook).filter(Webhook.id == webhook_id).first()
+        if not webhook:
+            return {
+                'success': False,
+                'message': 'Webhook not found',
+                'status_code': None
+            }
+
+        # Build test payload - use template if configured
+        if webhook.template:
+            template_service = get_template_service()
+            rendered, error = template_service.render_test_payload(
+                webhook.template,
+                webhook.template_format or 'json'
+            )
+
+            if error:
+                return {
+                    'success': False,
+                    'message': f'Template error: {error}',
+                    'status_code': None
+                }
+
+            # Determine content type
+            if webhook.content_type_override:
+                content_type = webhook.content_type_override
+            elif webhook.template_format == 'text':
+                content_type = 'text/plain'
+            else:
+                content_type = 'application/json'
+
+            # Parse JSON template
+            if webhook.template_format == 'json':
+                try:
+                    payload = json.loads(rendered)
+                except json.JSONDecodeError:
+                    return {
+                        'success': False,
+                        'message': 'Template rendered invalid JSON',
+                        'status_code': None
+                    }
+            else:
+                payload = rendered
+        else:
+            # Default test payload
+            payload = {
+                "event": "webhook.test",
+                "message": "This is a test webhook from SneakyScanner",
+                "timestamp": datetime.now(timezone.utc).isoformat(),
+                "webhook": {
+                    "id": webhook.id,
+                    "name": webhook.name
+                }
+            }
+            content_type = 'application/json'
+
+        # Prepare headers
+        headers = {'Content-Type': content_type}
+
+        if webhook.custom_headers:
+            try:
+                custom_headers = json.loads(webhook.custom_headers)
+                headers.update(custom_headers)
+            except json.JSONDecodeError:
+                pass
+
+        # Prepare authentication
+        auth = None
+        if webhook.auth_type == 'bearer' and webhook.auth_token:
+            decrypted_token = self._decrypt_value(webhook.auth_token)
+            headers['Authorization'] = f'Bearer {decrypted_token}'
+        elif webhook.auth_type == 'basic' and webhook.auth_token:
+            decrypted_token = self._decrypt_value(webhook.auth_token)
+            if ':' in decrypted_token:
+                username, password = decrypted_token.split(':', 1)
+                auth = HTTPBasicAuth(username, password)
+
+        # Execute test request
+        try:
+            timeout = webhook.timeout or 10
+
+            # Use appropriate parameter based on payload type
+            if isinstance(payload, dict):
+                # JSON payload
+                response = requests.post(
+                    webhook.url,
+                    json=payload,
+                    headers=headers,
+                    auth=auth,
+                    timeout=timeout
+                )
+            else:
+                # Text payload
+                response = requests.post(
+                    webhook.url,
+                    data=payload,
+                    headers=headers,
+                    auth=auth,
+                    timeout=timeout
+                )
+
+            return {
+                'success': response.status_code < 400,
+                'message': f'HTTP {response.status_code}',
+                'status_code': response.status_code,
+                'response_body': response.text[:500]
+            }
+
+        except requests.exceptions.Timeout:
+            return {
+                'success': False,
+                'message': f'Request timeout after {timeout} seconds',
+                'status_code': None
+            }
+
+        except requests.exceptions.ConnectionError as e:
+            return {
+                'success': False,
+                'message': f'Connection error: {str(e)}',
+                'status_code': None
+            }
+
+        except Exception as e:
+            return {
+                'success': False,
+                'message': f'Error: {str(e)}',
+                'status_code': None
+            }

app/web/static/css/config-manager.css

@@ -0,0 +1,507 @@
+/**
+ * Config Manager Styles
+ * Phase 4: Config Creator - CSS styling for config management UI
+ */
+
+/* ============================================
+   Dropzone Styling
+   ============================================ */
+
+.dropzone {
+    border: 2px dashed #6c757d;
+    border-radius: 8px;
+    padding: 40px 20px;
+    text-align: center;
+    cursor: pointer;
+    transition: all 0.3s ease;
+    background-color: #1e293b;
+    min-height: 200px;
+    display: flex;
+    flex-direction: column;
+    align-items: center;
+    justify-content: center;
+}
+
+.dropzone:hover {
+    border-color: #0d6efd;
+    background-color: #2d3748;
+}
+
+.dropzone.dragover {
+    border-color: #0d6efd;
+    background-color: #1a365d;
+    border-width: 3px;
+}
+
+.dropzone i {
+    font-size: 48px;
+    color: #94a3b8;
+    margin-bottom: 16px;
+    display: block;
+}
+
+.dropzone p {
+    color: #cbd5e0;
+    margin: 0;
+    font-size: 1rem;
+}
+
+.dropzone:hover i {
+    color: #0d6efd;
+}
+
+/* ============================================
+   Preview Pane Styling
+   ============================================ */
+
+#yaml-preview {
+    background-color: #1e293b;
+    border-radius: 8px;
+    padding: 16px;
+}
+
+#yaml-preview pre {
+    background-color: #0f172a;
+    border: 1px solid #334155;
+    border-radius: 6px;
+    padding: 16px;
+    max-height: 500px;
+    overflow-y: auto;
+    margin: 0;
+}
+
+#yaml-preview pre code {
+    color: #e2e8f0;
+    font-family: 'Monaco', 'Menlo', 'Ubuntu Mono', monospace;
+    font-size: 0.9rem;
+    line-height: 1.6;
+    white-space: pre;
+}
+
+#preview-placeholder {
+    background-color: #1e293b;
+    border: 2px dashed #475569;
+    border-radius: 8px;
+    padding: 60px 20px;
+    text-align: center;
+    color: #94a3b8;
+}
+
+#preview-placeholder i {
+    font-size: 3rem;
+    margin-bottom: 1rem;
+    display: block;
+    opacity: 0.5;
+}
+
+/* ============================================
+   Config Table Styling
+   ============================================ */
+
+#configs-table {
+    background-color: #1e293b;
+    border-radius: 8px;
+    overflow: hidden;
+}
+
+#configs-table thead {
+    background-color: #0f172a;
+    border-bottom: 2px solid #334155;
+}
+
+#configs-table thead th {
+    color: #cbd5e0;
+    font-weight: 600;
+    padding: 12px 16px;
+    border: none;
+}
+
+#configs-table tbody tr {
+    border-bottom: 1px solid #334155;
+    transition: background-color 0.2s ease;
+}
+
+#configs-table tbody tr:hover {
+    background-color: #2d3748;
+}
+
+#configs-table tbody td {
+    padding: 12px 16px;
+    color: #e2e8f0;
+    vertical-align: middle;
+    border: none;
+}
+
+#configs-table tbody td code {
+    background-color: #0f172a;
+    padding: 2px 6px;
+    border-radius: 4px;
+    color: #60a5fa;
+    font-size: 0.9rem;
+}
+
+/* ============================================
+   Action Buttons
+   ============================================ */
+
+.config-actions {
+    white-space: nowrap;
+}
+
+.config-actions .btn {
+    margin-right: 4px;
+    padding: 4px 8px;
+    font-size: 0.875rem;
+}
+
+.config-actions .btn:last-child {
+    margin-right: 0;
+}
+
+.config-actions .btn i {
+    font-size: 1rem;
+}
+
+/* Disabled button styling */
+.config-actions .btn:disabled {
+    opacity: 0.4;
+    cursor: not-allowed;
+}
+
+/* ============================================
+   Schedule Badge
+   ============================================ */
+
+.schedule-badge {
+    display: inline-block;
+    background-color: #3b82f6;
+    color: white;
+    padding: 4px 10px;
+    border-radius: 12px;
+    font-size: 0.8rem;
+    font-weight: 600;
+    min-width: 24px;
+    text-align: center;
+    cursor: help;
+}
+
+.schedule-badge:hover {
+    background-color: #2563eb;
+}
+
+/* ============================================
+   Search Box
+   ============================================ */
+
+#search {
+    background-color: #1e293b;
+    border: 1px solid #475569;
+    color: #e2e8f0;
+    padding: 8px 12px;
+    border-radius: 6px;
+    transition: border-color 0.2s ease;
+}
+
+#search:focus {
+    background-color: #0f172a;
+    border-color: #3b82f6;
+    color: #e2e8f0;
+    outline: none;
+    box-shadow: 0 0 0 3px rgba(59, 130, 246, 0.1);
+}
+
+#search::placeholder {
+    color: #64748b;
+}
+
+/* ============================================
+   Alert Messages
+   ============================================ */
+
+.alert {
+    border-radius: 8px;
+    padding: 12px 16px;
+    margin-bottom: 16px;
+}
+
+.alert-danger {
+    background-color: #7f1d1d;
+    border: 1px solid #991b1b;
+    color: #fecaca;
+}
+
+.alert-success {
+    background-color: #14532d;
+    border: 1px solid #166534;
+    color: #86efac;
+}
+
+.alert i {
+    margin-right: 8px;
+}
+
+/* ============================================
+   Card Styling
+   ============================================ */
+
+.card {
+    background-color: #1e293b;
+    border: 1px solid #334155;
+    border-radius: 8px;
+    margin-bottom: 20px;
+}
+
+.card-body {
+    padding: 20px;
+}
+
+.card h5 {
+    color: #cbd5e0;
+    margin-bottom: 16px;
+}
+
+.card .text-muted {
+    color: #94a3b8 !important;
+}
+
+/* ============================================
+   Tab Navigation
+   ============================================ */
+
+.nav-tabs {
+    border-bottom: 2px solid #334155;
+}
+
+.nav-tabs .nav-link {
+    color: #94a3b8;
+    border: none;
+    border-bottom: 2px solid transparent;
+    padding: 12px 20px;
+    transition: all 0.2s ease;
+}
+
+.nav-tabs .nav-link:hover {
+    color: #cbd5e0;
+    background-color: #2d3748;
+    border-color: transparent;
+}
+
+.nav-tabs .nav-link.active {
+    color: #60a5fa;
+    background-color: transparent;
+    border-color: transparent transparent #60a5fa transparent;
+}
+
+/* ============================================
+   Buttons
+   ============================================ */
+
+.btn {
+    border-radius: 6px;
+    padding: 8px 16px;
+    font-weight: 500;
+    transition: all 0.2s ease;
+}
+
+.btn-primary {
+    background-color: #3b82f6;
+    border-color: #3b82f6;
+}
+
+.btn-primary:hover {
+    background-color: #2563eb;
+    border-color: #2563eb;
+}
+
+.btn-success {
+    background-color: #22c55e;
+    border-color: #22c55e;
+}
+
+.btn-success:hover {
+    background-color: #16a34a;
+    border-color: #16a34a;
+}
+
+.btn-outline-secondary {
+    color: #94a3b8;
+    border-color: #475569;
+}
+
+.btn-outline-secondary:hover {
+    background-color: #475569;
+    border-color: #475569;
+    color: #e2e8f0;
+}
+
+.btn-outline-primary {
+    color: #60a5fa;
+    border-color: #3b82f6;
+}
+
+.btn-outline-primary:hover {
+    background-color: #3b82f6;
+    border-color: #3b82f6;
+    color: white;
+}
+
+.btn-outline-danger {
+    color: #f87171;
+    border-color: #dc2626;
+}
+
+.btn-outline-danger:hover {
+    background-color: #dc2626;
+    border-color: #dc2626;
+    color: white;
+}
+
+/* ============================================
+   Modal Styling
+   ============================================ */
+
+.modal-content {
+    background-color: #1e293b;
+    border: 1px solid #334155;
+    color: #e2e8f0;
+}
+
+.modal-header {
+    border-bottom: 1px solid #334155;
+}
+
+.modal-footer {
+    border-top: 1px solid #334155;
+}
+
+.modal-title {
+    color: #cbd5e0;
+}
+
+.btn-close {
+    filter: invert(1);
+}
+
+/* ============================================
+   Spinner/Loading
+   ============================================ */
+
+.spinner-border {
+    color: #3b82f6;
+}
+
+/* ============================================
+   Responsive Adjustments
+   ============================================ */
+
+@media (max-width: 768px) {
+    #configs-table {
+        font-size: 0.875rem;
+    }
+
+    #configs-table thead th,
+    #configs-table tbody td {
+        padding: 8px 12px;
+    }
+
+    .config-actions .btn {
+        padding: 2px 6px;
+        margin-right: 2px;
+    }
+
+    .config-actions .btn i {
+        font-size: 0.9rem;
+    }
+
+    .dropzone {
+        padding: 30px 15px;
+        min-height: 150px;
+    }
+
+    .dropzone i {
+        font-size: 36px;
+    }
+
+    #yaml-preview pre {
+        max-height: 300px;
+        font-size: 0.8rem;
+    }
+}
+
+@media (max-width: 576px) {
+    /* Stack table cells on very small screens */
+    #configs-table thead {
+        display: none;
+    }
+
+    #configs-table tbody tr {
+        display: block;
+        margin-bottom: 16px;
+        border: 1px solid #334155;
+        border-radius: 8px;
+        padding: 12px;
+    }
+
+    #configs-table tbody td {
+        display: block;
+        text-align: left;
+        padding: 6px 0;
+        border: none;
+    }
+
+    #configs-table tbody td:before {
+        content: attr(data-label);
+        font-weight: 600;
+        color: #94a3b8;
+        display: inline-block;
+        width: 100px;
+    }
+
+    .config-actions {
+        margin-top: 8px;
+    }
+}
+
+/* ============================================
+   Utility Classes
+   ============================================ */
+
+.text-center {
+    text-align: center;
+}
+
+.py-4 {
+    padding-top: 1.5rem;
+    padding-bottom: 1.5rem;
+}
+
+.py-5 {
+    padding-top: 3rem;
+    padding-bottom: 3rem;
+}
+
+.mt-2 {
+    margin-top: 0.5rem;
+}
+
+.mt-3 {
+    margin-top: 1rem;
+}
+
+.mb-3 {
+    margin-bottom: 1rem;
+}
+
+.mb-4 {
+    margin-bottom: 1.5rem;
+}
+
+/* ============================================
+   Result Count Display
+   ============================================ */
+
+#result-count {
+    color: #94a3b8;
+    font-size: 0.9rem;
+    font-weight: 500;
+}

app/web/static/js/config-manager.js

@@ -0,0 +1,633 @@
+/**
+ * Config Manager - Handles configuration file upload, management, and display
+ * Phase 4: Config Creator
+ */
+
+class ConfigManager {
+    constructor() {
+        this.apiBase = '/api/configs';
+        this.currentPreview = null;
+        this.currentFilename = null;
+    }
+
+    /**
+     * Load all configurations and populate the table
+     */
+    async loadConfigs() {
+        try {
+            const response = await fetch(this.apiBase);
+
+            if (!response.ok) {
+                throw new Error(`HTTP ${response.status}: ${response.statusText}`);
+            }
+
+            const data = await response.json();
+            this.renderConfigsTable(data.configs || []);
+            return data.configs;
+        } catch (error) {
+            console.error('Error loading configs:', error);
+            this.showError('Failed to load configurations: ' + error.message);
+            return [];
+        }
+    }
+
+    /**
+     * Get a specific configuration file
+     */
+    async getConfig(filename) {
+        try {
+            const response = await fetch(`${this.apiBase}/${encodeURIComponent(filename)}`);
+
+            if (!response.ok) {
+                throw new Error(`HTTP ${response.status}: ${response.statusText}`);
+            }
+
+            return await response.json();
+        } catch (error) {
+            console.error('Error getting config:', error);
+            this.showError('Failed to load configuration: ' + error.message);
+            throw error;
+        }
+    }
+
+    /**
+     * Upload CSV file and convert to YAML
+     */
+    async uploadCSV(file) {
+        const formData = new FormData();
+        formData.append('file', file);
+
+        try {
+            const response = await fetch(`${this.apiBase}/upload-csv`, {
+                method: 'POST',
+                body: formData
+            });
+
+            const data = await response.json();
+
+            if (!response.ok) {
+                throw new Error(data.message || `HTTP ${response.status}: ${response.statusText}`);
+            }
+
+            return data;
+        } catch (error) {
+            console.error('Error uploading CSV:', error);
+            throw error;
+        }
+    }
+
+    /**
+     * Upload YAML file directly
+     */
+    async uploadYAML(file, filename = null) {
+        const formData = new FormData();
+        formData.append('file', file);
+
+        if (filename) {
+            formData.append('filename', filename);
+        }
+
+        try {
+            const response = await fetch(`${this.apiBase}/upload-yaml`, {
+                method: 'POST',
+                body: formData
+            });
+
+            const data = await response.json();
+
+            if (!response.ok) {
+                throw new Error(data.message || `HTTP ${response.status}: ${response.statusText}`);
+            }
+
+            return data;
+        } catch (error) {
+            console.error('Error uploading YAML:', error);
+            throw error;
+        }
+    }
+
+    /**
+     * Delete a configuration file
+     */
+    async deleteConfig(filename) {
+        try {
+            const response = await fetch(`${this.apiBase}/${encodeURIComponent(filename)}`, {
+                method: 'DELETE'
+            });
+
+            const data = await response.json();
+
+            if (!response.ok) {
+                throw new Error(data.message || `HTTP ${response.status}: ${response.statusText}`);
+            }
+
+            return data;
+        } catch (error) {
+            console.error('Error deleting config:', error);
+            throw error;
+        }
+    }
+
+    /**
+     * Download CSV template
+     */
+    downloadTemplate() {
+        window.location.href = `${this.apiBase}/template`;
+    }
+
+    /**
+     * Download a specific config file
+     */
+    downloadConfig(filename) {
+        window.location.href = `${this.apiBase}/${encodeURIComponent(filename)}/download`;
+    }
+
+    /**
+     * Show YAML preview in the preview pane
+     */
+    showPreview(yamlContent, filename = null) {
+        this.currentPreview = yamlContent;
+        this.currentFilename = filename;
+
+        const previewElement = document.getElementById('yaml-preview');
+        const contentElement = document.getElementById('yaml-content');
+        const placeholderElement = document.getElementById('preview-placeholder');
+
+        if (contentElement) {
+            contentElement.textContent = yamlContent;
+        }
+
+        if (previewElement) {
+            previewElement.style.display = 'block';
+        }
+
+        if (placeholderElement) {
+            placeholderElement.style.display = 'none';
+        }
+
+        // Enable save button
+        const saveBtn = document.getElementById('save-config-btn');
+        if (saveBtn) {
+            saveBtn.disabled = false;
+        }
+    }
+
+    /**
+     * Hide YAML preview
+     */
+    hidePreview() {
+        this.currentPreview = null;
+        this.currentFilename = null;
+
+        const previewElement = document.getElementById('yaml-preview');
+        const placeholderElement = document.getElementById('preview-placeholder');
+
+        if (previewElement) {
+            previewElement.style.display = 'none';
+        }
+
+        if (placeholderElement) {
+            placeholderElement.style.display = 'block';
+        }
+
+        // Disable save button
+        const saveBtn = document.getElementById('save-config-btn');
+        if (saveBtn) {
+            saveBtn.disabled = true;
+        }
+    }
+
+    /**
+     * Render configurations table
+     */
+    renderConfigsTable(configs) {
+        const tbody = document.querySelector('#configs-table tbody');
+
+        if (!tbody) {
+            console.warn('Configs table body not found');
+            return;
+        }
+
+        // Clear existing rows
+        tbody.innerHTML = '';
+
+        if (configs.length === 0) {
+            tbody.innerHTML = `
+                <tr>
+                    <td colspan="6" class="text-center text-muted py-4">
+                        <i class="bi bi-inbox" style="font-size: 2rem;"></i>
+                        <p class="mt-2">No configuration files found. Create your first config!</p>
+                    </td>
+                </tr>
+            `;
+            return;
+        }
+
+        // Populate table
+        configs.forEach(config => {
+            const row = document.createElement('tr');
+            row.dataset.filename = config.filename;
+
+            // Format date
+            const createdDate = config.created_at ?
+                new Date(config.created_at).toLocaleDateString('en-US', {
+                    year: 'numeric',
+                    month: 'short',
+                    day: 'numeric'
+                }) : 'Unknown';
+
+            // Format file size
+            const fileSize = config.size_bytes ?
+                this.formatFileSize(config.size_bytes) : 'Unknown';
+
+            // Schedule usage badge
+            const scheduleCount = config.used_by_schedules ? config.used_by_schedules.length : 0;
+            const scheduleBadge = scheduleCount > 0 ?
+                `<span class="schedule-badge" title="${config.used_by_schedules.join(', ')}">${scheduleCount}</span>` :
+                '<span class="text-muted">None</span>';
+
+            row.innerHTML = `
+                <td><code>${this.escapeHtml(config.filename)}</code></td>
+                <td>${this.escapeHtml(config.title || 'Untitled')}</td>
+                <td>${createdDate}</td>
+                <td>${fileSize}</td>
+                <td>${scheduleBadge}</td>
+                <td class="config-actions">
+                    <button class="btn btn-sm btn-outline-secondary"
+                            onclick="configManager.viewConfig('${this.escapeHtml(config.filename)}')"
+                            title="View config">
+                        <i class="bi bi-eye"></i>
+                    </button>
+                    <button class="btn btn-sm btn-outline-primary"
+                            onclick="configManager.downloadConfig('${this.escapeHtml(config.filename)}')"
+                            title="Download config">
+                        <i class="bi bi-download"></i>
+                    </button>
+                    <button class="btn btn-sm btn-outline-danger"
+                            onclick="configManager.confirmDelete('${this.escapeHtml(config.filename)}', ${scheduleCount})"
+                            title="Delete config"
+                            ${scheduleCount > 0 ? 'disabled' : ''}>
+                        <i class="bi bi-trash"></i>
+                    </button>
+                </td>
+            `;
+
+            tbody.appendChild(row);
+        });
+
+        // Update result count
+        this.updateResultCount(configs.length);
+    }
+
+    /**
+     * View/preview a configuration file
+     */
+    async viewConfig(filename) {
+        try {
+            const config = await this.getConfig(filename);
+
+            // Show modal with config content
+            const modalHtml = `
+                <div class="modal fade" id="viewConfigModal" tabindex="-1">
+                    <div class="modal-dialog modal-lg">
+                        <div class="modal-content">
+                            <div class="modal-header">
+                                <h5 class="modal-title">${this.escapeHtml(filename)}</h5>
+                                <button type="button" class="btn-close" data-bs-dismiss="modal"></button>
+                            </div>
+                            <div class="modal-body">
+                                <pre><code class="language-yaml">${this.escapeHtml(config.content)}</code></pre>
+                            </div>
+                            <div class="modal-footer">
+                                <button type="button" class="btn btn-secondary" data-bs-dismiss="modal">Close</button>
+                                <button type="button" class="btn btn-primary"
+                                        onclick="configManager.downloadConfig('${this.escapeHtml(filename)}')">
+                                    <i class="bi bi-download"></i> Download
+                                </button>
+                            </div>
+                        </div>
+                    </div>
+                </div>
+            `;
+
+            // Remove existing modal if any
+            const existingModal = document.getElementById('viewConfigModal');
+            if (existingModal) {
+                existingModal.remove();
+            }
+
+            // Add modal to page
+            document.body.insertAdjacentHTML('beforeend', modalHtml);
+
+            // Show modal
+            const modal = new bootstrap.Modal(document.getElementById('viewConfigModal'));
+            modal.show();
+
+            // Clean up on close
+            document.getElementById('viewConfigModal').addEventListener('hidden.bs.modal', function() {
+                this.remove();
+            });
+
+        } catch (error) {
+            this.showError('Failed to view configuration: ' + error.message);
+        }
+    }
+
+    /**
+     * Confirm deletion of a configuration
+     */
+    confirmDelete(filename, scheduleCount) {
+        if (scheduleCount > 0) {
+            this.showError(`Cannot delete "${filename}" - it is used by ${scheduleCount} schedule(s)`);
+            return;
+        }
+
+        if (confirm(`Are you sure you want to delete "${filename}"?\n\nThis action cannot be undone.`)) {
+            this.performDelete(filename);
+        }
+    }
+
+    /**
+     * Perform the actual deletion
+     */
+    async performDelete(filename) {
+        try {
+            await this.deleteConfig(filename);
+            this.showSuccess(`Configuration "${filename}" deleted successfully`);
+
+            // Reload configs table
+            await this.loadConfigs();
+        } catch (error) {
+            this.showError('Failed to delete configuration: ' + error.message);
+        }
+    }
+
+    /**
+     * Filter configs table by search term
+     */
+    filterConfigs(searchTerm) {
+        const term = searchTerm.toLowerCase().trim();
+        const rows = document.querySelectorAll('#configs-table tbody tr');
+        let visibleCount = 0;
+
+        rows.forEach(row => {
+            // Skip empty state row
+            if (row.querySelector('td[colspan]')) {
+                return;
+            }
+
+            const filename = row.cells[0]?.textContent.toLowerCase() || '';
+            const title = row.cells[1]?.textContent.toLowerCase() || '';
+
+            const matches = filename.includes(term) || title.includes(term);
+
+            row.style.display = matches ? '' : 'none';
+            if (matches) visibleCount++;
+        });
+
+        this.updateResultCount(visibleCount);
+    }
+
+    /**
+     * Update result count display
+     */
+    updateResultCount(count) {
+        const countElement = document.getElementById('result-count');
+        if (countElement) {
+            countElement.textContent = `${count} config${count !== 1 ? 's' : ''}`;
+        }
+    }
+
+    /**
+     * Show error message
+     */
+    showError(message, elementId = 'error-display') {
+        const errorElement = document.getElementById(elementId);
+        if (errorElement) {
+            errorElement.innerHTML = `
+                <div class="alert alert-danger alert-dismissible fade show" role="alert">
+                    <i class="bi bi-exclamation-triangle"></i> ${this.escapeHtml(message)}
+                    <button type="button" class="btn-close" data-bs-dismiss="alert"></button>
+                </div>
+            `;
+            errorElement.scrollIntoView({ behavior: 'smooth', block: 'nearest' });
+        } else {
+            console.error('Error:', message);
+            alert('Error: ' + message);
+        }
+    }
+
+    /**
+     * Show success message
+     */
+    showSuccess(message, elementId = 'success-display') {
+        const successElement = document.getElementById(elementId);
+        if (successElement) {
+            successElement.innerHTML = `
+                <div class="alert alert-success alert-dismissible fade show" role="alert">
+                    <i class="bi bi-check-circle"></i> ${this.escapeHtml(message)}
+                    <button type="button" class="btn-close" data-bs-dismiss="alert"></button>
+                </div>
+            `;
+            successElement.scrollIntoView({ behavior: 'smooth', block: 'nearest' });
+        } else {
+            console.log('Success:', message);
+        }
+    }
+
+    /**
+     * Clear all messages
+     */
+    clearMessages() {
+        const elements = ['error-display', 'success-display', 'csv-errors', 'yaml-errors'];
+        elements.forEach(id => {
+            const element = document.getElementById(id);
+            if (element) {
+                element.innerHTML = '';
+            }
+        });
+    }
+
+    /**
+     * Format file size for display
+     */
+    formatFileSize(bytes) {
+        if (bytes === 0) return '0 Bytes';
+        const k = 1024;
+        const sizes = ['Bytes', 'KB', 'MB'];
+        const i = Math.floor(Math.log(bytes) / Math.log(k));
+        return Math.round(bytes / Math.pow(k, i) * 100) / 100 + ' ' + sizes[i];
+    }
+
+    /**
+     * Escape HTML to prevent XSS
+     */
+    escapeHtml(text) {
+        const div = document.createElement('div');
+        div.textContent = text;
+        return div.innerHTML;
+    }
+}
+
+// Initialize global config manager instance
+const configManager = new ConfigManager();
+
+/**
+ * Setup drag-and-drop zone for file uploads
+ */
+function setupDropzone(dropzoneId, fileInputId, fileType, onUploadCallback) {
+    const dropzone = document.getElementById(dropzoneId);
+    const fileInput = document.getElementById(fileInputId);
+
+    if (!dropzone || !fileInput) {
+        console.warn(`Dropzone setup failed: missing elements (${dropzoneId}, ${fileInputId})`);
+        return;
+    }
+
+    // Click to browse
+    dropzone.addEventListener('click', () => {
+        fileInput.click();
+    });
+
+    // Drag over
+    dropzone.addEventListener('dragover', (e) => {
+        e.preventDefault();
+        e.stopPropagation();
+        dropzone.classList.add('dragover');
+    });
+
+    // Drag leave
+    dropzone.addEventListener('dragleave', (e) => {
+        e.preventDefault();
+        e.stopPropagation();
+        dropzone.classList.remove('dragover');
+    });
+
+    // Drop
+    dropzone.addEventListener('drop', (e) => {
+        e.preventDefault();
+        e.stopPropagation();
+        dropzone.classList.remove('dragover');
+
+        const files = e.dataTransfer.files;
+        if (files.length > 0) {
+            handleFileUpload(files[0], fileType, onUploadCallback);
+        }
+    });
+
+    // File input change
+    fileInput.addEventListener('change', (e) => {
+        const files = e.target.files;
+        if (files.length > 0) {
+            handleFileUpload(files[0], fileType, onUploadCallback);
+        }
+    });
+}
+
+/**
+ * Handle file upload (CSV or YAML)
+ */
+async function handleFileUpload(file, fileType, callback) {
+    configManager.clearMessages();
+
+    // Validate file type
+    const extension = file.name.split('.').pop().toLowerCase();
+
+    if (fileType === 'csv' && extension !== 'csv') {
+        configManager.showError('Please upload a CSV file (.csv)', 'csv-errors');
+        return;
+    }
+
+    if (fileType === 'yaml' && !['yaml', 'yml'].includes(extension)) {
+        configManager.showError('Please upload a YAML file (.yaml or .yml)', 'yaml-errors');
+        return;
+    }
+
+    // Validate file size (2MB limit for configs)
+    const maxSize = 2 * 1024 * 1024; // 2MB
+    if (file.size > maxSize) {
+        const errorId = fileType === 'csv' ? 'csv-errors' : 'yaml-errors';
+        configManager.showError(`File too large (${configManager.formatFileSize(file.size)}). Maximum size is 2MB.`, errorId);
+        return;
+    }
+
+    // Call the provided callback
+    if (callback) {
+        try {
+            await callback(file);
+        } catch (error) {
+            const errorId = fileType === 'csv' ? 'csv-errors' : 'yaml-errors';
+            configManager.showError(error.message, errorId);
+        }
+    }
+}
+
+/**
+ * Handle CSV upload and preview
+ */
+async function handleCSVUpload(file) {
+    try {
+        // Show loading state
+        const previewPlaceholder = document.getElementById('preview-placeholder');
+        if (previewPlaceholder) {
+            previewPlaceholder.innerHTML = '<div class="spinner-border" role="status"><span class="visually-hidden">Loading...</span></div>';
+        }
+
+        // Upload CSV
+        const result = await configManager.uploadCSV(file);
+
+        // Show preview
+        configManager.showPreview(result.preview, result.filename);
+
+        // Show success message
+        configManager.showSuccess(`CSV uploaded successfully! Preview the generated YAML below.`, 'csv-errors');
+
+    } catch (error) {
+        configManager.hidePreview();
+        throw error;
+    }
+}
+
+/**
+ * Handle YAML upload
+ */
+async function handleYAMLUpload(file) {
+    try {
+        // Upload YAML
+        const result = await configManager.uploadYAML(file);
+
+        // Show success and redirect
+        configManager.showSuccess(`Configuration "${result.filename}" uploaded successfully!`, 'yaml-errors');
+
+        // Redirect to configs list after 2 seconds
+        setTimeout(() => {
+            window.location.href = '/configs';
+        }, 2000);
+
+    } catch (error) {
+        throw error;
+    }
+}
+
+/**
+ * Save the previewed configuration (after CSV upload)
+ */
+async function savePreviewedConfig() {
+    if (!configManager.currentPreview || !configManager.currentFilename) {
+        configManager.showError('No configuration to save', 'csv-errors');
+        return;
+    }
+
+    try {
+        // The config is already saved during CSV upload, just redirect
+        configManager.showSuccess(`Configuration "${configManager.currentFilename}" saved successfully!`, 'csv-errors');
+
+        // Redirect to configs list after 2 seconds
+        setTimeout(() => {
+            window.location.href = '/configs';
+        }, 2000);
+
+    } catch (error) {
+        configManager.showError('Failed to save configuration: ' + error.message, 'csv-errors');
+    }
+}

app/web/templates/alert_rules.html

@@ -0,0 +1,505 @@
+{% extends "base.html" %}
+
+{% block title %}Alert Rules - SneakyScanner{% endblock %}
+
+{% block content %}
+<div class="row mt-4">
+    <div class="col-12 d-flex justify-content-between align-items-center mb-4">
+        <h1>Alert Rules</h1>
+        <div>
+            <a href="{{ url_for('main.alerts') }}" class="btn btn-outline-primary me-2">
+                <i class="bi bi-bell"></i> View Alerts
+            </a>
+            <button class="btn btn-primary" onclick="showCreateRuleModal()">
+                <i class="bi bi-plus-circle"></i> Create Rule
+            </button>
+        </div>
+    </div>
+</div>
+
+<!-- Rule Statistics -->
+<div class="row mb-4">
+    <div class="col-md-6 mb-3">
+        <div class="card">
+            <div class="card-body">
+                <h6 class="text-muted mb-2">Total Rules</h6>
+                <h3 class="mb-0">{{ rules | length }}</h3>
+            </div>
+        </div>
+    </div>
+    <div class="col-md-6 mb-3">
+        <div class="card">
+            <div class="card-body">
+                <h6 class="text-muted mb-2">Active Rules</h6>
+                <h3 class="mb-0 text-success">{{ rules | selectattr('enabled') | list | length }}</h3>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Rules Table -->
+<div class="row">
+    <div class="col-12">
+        <div class="card">
+            <div class="card-header">
+                <h5 class="mb-0">Alert Rules Configuration</h5>
+            </div>
+            <div class="card-body">
+                {% if rules %}
+                <div class="table-responsive">
+                    <table class="table table-hover">
+                        <thead>
+                            <tr>
+                                <th>Name</th>
+                                <th>Type</th>
+                                <th>Severity</th>
+                                <th>Threshold</th>
+                                <th>Config</th>
+                                <th>Notifications</th>
+                                <th>Status</th>
+                                <th>Actions</th>
+                            </tr>
+                        </thead>
+                        <tbody>
+                            {% for rule in rules %}
+                            <tr>
+                                <td>
+                                    <strong>{{ rule.name or 'Unnamed Rule' }}</strong>
+                                    <br>
+                                    <small class="text-muted">ID: {{ rule.id }}</small>
+                                </td>
+                                <td>
+                                    <span class="badge bg-secondary">
+                                        {{ rule.rule_type.replace('_', ' ').title() }}
+                                    </span>
+                                </td>
+                                <td>
+                                    {% if rule.severity == 'critical' %}
+                                    <span class="badge bg-danger">Critical</span>
+                                    {% elif rule.severity == 'warning' %}
+                                    <span class="badge bg-warning">Warning</span>
+                                    {% else %}
+                                    <span class="badge bg-info">{{ rule.severity or 'Info' }}</span>
+                                    {% endif %}
+                                </td>
+                                <td>
+                                    {% if rule.threshold %}
+                                        {% if rule.rule_type == 'cert_expiry' %}
+                                            {{ rule.threshold }} days
+                                        {% elif rule.rule_type == 'drift_detection' %}
+                                            {{ rule.threshold }}%
+                                        {% else %}
+                                            {{ rule.threshold }}
+                                        {% endif %}
+                                    {% else %}
+                                        <span class="text-muted">-</span>
+                                    {% endif %}
+                                </td>
+                                <td>
+                                    {% if rule.config %}
+                                        <small class="text-muted">{{ rule.config.title }}</small>
+                                    {% else %}
+                                        <span class="badge bg-primary">All Configs</span>
+                                    {% endif %}
+                                </td>
+                                <td>
+                                    {% if rule.email_enabled %}
+                                        <i class="bi bi-envelope-fill text-primary" title="Email enabled"></i>
+                                    {% endif %}
+                                    {% if rule.webhook_enabled %}
+                                        <i class="bi bi-send-fill text-primary" title="Webhook enabled"></i>
+                                    {% endif %}
+                                    {% if not rule.email_enabled and not rule.webhook_enabled %}
+                                        <span class="text-muted">None</span>
+                                    {% endif %}
+                                </td>
+                                <td>
+                                    <div class="form-check form-switch">
+                                        <input class="form-check-input" type="checkbox"
+                                               id="rule-enabled-{{ rule.id }}"
+                                               {% if rule.enabled %}checked{% endif %}
+                                               onchange="toggleRule({{ rule.id }}, this.checked)">
+                                        <label class="form-check-label" for="rule-enabled-{{ rule.id }}">
+                                            {% if rule.enabled %}
+                                                <span class="text-success ms-2">Active</span>
+                                            {% else %}
+                                                <span class="text-muted ms-2">Inactive</span>
+                                            {% endif %}
+                                        </label>
+                                    </div>
+                                </td>
+                                <td>
+                                    <button class="btn btn-sm btn-outline-primary" onclick="editRule({{ rule.id }})">
+                                        <i class="bi bi-pencil"></i>
+                                    </button>
+                                    <button class="btn btn-sm btn-outline-danger" onclick="deleteRule({{ rule.id }}, '{{ rule.name }}')">
+                                        <i class="bi bi-trash"></i>
+                                    </button>
+                                </td>
+                            </tr>
+                            {% endfor %}
+                        </tbody>
+                    </table>
+                </div>
+                {% else %}
+                <div class="text-center py-5 text-muted">
+                    <i class="bi bi-bell-slash" style="font-size: 3rem;"></i>
+                    <h5 class="mt-3">No alert rules configured</h5>
+                    <p>Create alert rules to be notified of important scan findings.</p>
+                    <button class="btn btn-primary mt-3" onclick="showCreateRuleModal()">
+                        <i class="bi bi-plus-circle"></i> Create Your First Rule
+                    </button>
+                </div>
+                {% endif %}
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Create/Edit Rule Modal -->
+<div class="modal fade" id="ruleModal" tabindex="-1">
+    <div class="modal-dialog modal-lg">
+        <div class="modal-content">
+            <div class="modal-header">
+                <h5 class="modal-title" id="ruleModalTitle">Create Alert Rule</h5>
+                <button type="button" class="btn-close" data-bs-dismiss="modal"></button>
+            </div>
+            <div class="modal-body">
+                <form id="ruleForm">
+                    <input type="hidden" id="rule-id">
+
+                    <div class="row">
+                        <div class="col-md-6 mb-3">
+                            <label for="rule-name" class="form-label">Rule Name</label>
+                            <input type="text" class="form-control" id="rule-name" required>
+                        </div>
+                        <div class="col-md-6 mb-3">
+                            <label for="rule-type" class="form-label">Rule Type</label>
+                            <select class="form-select" id="rule-type" required onchange="updateThresholdLabel()">
+                                <option value="">Select a type...</option>
+                                <option value="unexpected_port">Unexpected Port Detection</option>
+                                <option value="drift_detection">Drift Detection</option>
+                                <option value="cert_expiry">Certificate Expiry</option>
+                                <option value="weak_tls">Weak TLS Version</option>
+                                <option value="ping_failed">Ping Failed</option>
+                            </select>
+                        </div>
+                    </div>
+
+                    <div class="row">
+                        <div class="col-md-6 mb-3">
+                            <label for="rule-severity" class="form-label">Severity</label>
+                            <select class="form-select" id="rule-severity" required>
+                                <option value="info">Info</option>
+                                <option value="warning" selected>Warning</option>
+                                <option value="critical">Critical</option>
+                            </select>
+                        </div>
+                        <div class="col-md-6 mb-3">
+                            <label for="rule-threshold" class="form-label" id="threshold-label">Threshold</label>
+                            <input type="number" class="form-control" id="rule-threshold">
+                            <small class="form-text text-muted" id="threshold-help">
+                                Numeric value that triggers the alert (varies by rule type)
+                            </small>
+                        </div>
+                    </div>
+
+                    <div class="row">
+                        <div class="col-md-12 mb-3">
+                            <label for="rule-config" class="form-label">Apply to Config (optional)</label>
+                            <select class="form-select" id="rule-config">
+                                <option value="">All Configs (Apply to all scans)</option>
+                            </select>
+                            <small class="form-text text-muted" id="config-help-text">
+                                Select a specific config to limit this rule, or leave as "All Configs" to apply to all scans
+                            </small>
+                        </div>
+                    </div>
+
+                    <div class="row">
+                        <div class="col-md-6">
+                            <div class="form-check">
+                                <input class="form-check-input" type="checkbox" id="rule-email">
+                                <label class="form-check-label" for="rule-email">
+                                    Send Email Notifications
+                                </label>
+                            </div>
+                        </div>
+                        <div class="col-md-6">
+                            <div class="form-check">
+                                <input class="form-check-input" type="checkbox" id="rule-webhook">
+                                <label class="form-check-label" for="rule-webhook">
+                                    Send Webhook Notifications
+                                </label>
+                            </div>
+                        </div>
+                    </div>
+
+                    <div class="row mt-3">
+                        <div class="col-12">
+                            <div class="form-check">
+                                <input class="form-check-input" type="checkbox" id="rule-enabled" checked>
+                                <label class="form-check-label" for="rule-enabled">
+                                    Enable this rule immediately
+                                </label>
+                            </div>
+                        </div>
+                    </div>
+                </form>
+            </div>
+            <div class="modal-footer">
+                <button type="button" class="btn btn-secondary" data-bs-dismiss="modal">Cancel</button>
+                <button type="button" class="btn btn-primary" onclick="saveRule()">
+                    <span id="save-rule-text">Create Rule</span>
+                    <span id="save-rule-spinner" class="spinner-border spinner-border-sm ms-2" style="display: none;"></span>
+                </button>
+            </div>
+        </div>
+    </div>
+</div>
+
+<script>
+let editingRuleId = null;
+
+// Load available configs for the dropdown
+async function loadConfigsForRule() {
+    const selectEl = document.getElementById('rule-config');
+
+    try {
+        const response = await fetch('/api/configs');
+        if (!response.ok) {
+            throw new Error('Failed to load configurations');
+        }
+
+        const data = await response.json();
+        const configs = data.configs || [];
+
+        // Preserve the "All Configs" option and current selection
+        const currentValue = selectEl.value;
+        selectEl.innerHTML = '<option value="">All Configs (Apply to all scans)</option>';
+
+        configs.forEach(config => {
+            const option = document.createElement('option');
+            // Store the config ID as the value
+            option.value = config.id;
+            const siteText = config.site_count === 1 ? 'site' : 'sites';
+            option.textContent = `${config.title} (${config.site_count} ${siteText})`;
+            selectEl.appendChild(option);
+        });
+
+        // Restore selection if it was set
+        if (currentValue) {
+            selectEl.value = currentValue;
+        }
+    } catch (error) {
+        console.error('Error loading configs:', error);
+    }
+}
+
+function showCreateRuleModal() {
+    editingRuleId = null;
+    document.getElementById('ruleModalTitle').textContent = 'Create Alert Rule';
+    document.getElementById('save-rule-text').textContent = 'Create Rule';
+    document.getElementById('ruleForm').reset();
+    document.getElementById('rule-enabled').checked = true;
+
+    // Load configs when modal is shown
+    loadConfigsForRule();
+
+    new bootstrap.Modal(document.getElementById('ruleModal')).show();
+}
+
+function editRule(ruleId) {
+    editingRuleId = ruleId;
+    document.getElementById('ruleModalTitle').textContent = 'Edit Alert Rule';
+    document.getElementById('save-rule-text').textContent = 'Update Rule';
+
+    // Load configs first, then fetch rule details
+    loadConfigsForRule().then(() => {
+        // Fetch rule details
+        fetch(`/api/alerts/rules`, {
+            headers: {
+                'X-API-Key': localStorage.getItem('api_key') || ''
+            }
+        })
+        .then(response => response.json())
+        .then(data => {
+            const rule = data.rules.find(r => r.id === ruleId);
+            if (rule) {
+                document.getElementById('rule-id').value = rule.id;
+                document.getElementById('rule-name').value = rule.name || '';
+                document.getElementById('rule-type').value = rule.rule_type;
+                document.getElementById('rule-severity').value = rule.severity || 'warning';
+                document.getElementById('rule-threshold').value = rule.threshold || '';
+                document.getElementById('rule-config').value = rule.config_id || '';
+                document.getElementById('rule-email').checked = rule.email_enabled;
+                document.getElementById('rule-webhook').checked = rule.webhook_enabled;
+                document.getElementById('rule-enabled').checked = rule.enabled;
+
+                updateThresholdLabel();
+                new bootstrap.Modal(document.getElementById('ruleModal')).show();
+            }
+        })
+        .catch(error => {
+            console.error('Error fetching rule:', error);
+            alert('Failed to load rule details');
+        });
+    });
+}
+
+function updateThresholdLabel() {
+    const ruleType = document.getElementById('rule-type').value;
+    const label = document.getElementById('threshold-label');
+    const help = document.getElementById('threshold-help');
+
+    switch(ruleType) {
+        case 'cert_expiry':
+            label.textContent = 'Days Before Expiry';
+            help.textContent = 'Alert when certificate expires within this many days (default: 30)';
+            break;
+        case 'drift_detection':
+            label.textContent = 'Drift Percentage';
+            help.textContent = 'Alert when drift exceeds this percentage (0-100, default: 5)';
+            break;
+        case 'unexpected_port':
+            label.textContent = 'Threshold (optional)';
+            help.textContent = 'Leave blank - this rule alerts on any port not in your config file';
+            break;
+        case 'weak_tls':
+            label.textContent = 'Threshold (optional)';
+            help.textContent = 'Leave blank - this rule alerts on TLS versions below 1.2';
+            break;
+        case 'ping_failed':
+            label.textContent = 'Threshold (optional)';
+            help.textContent = 'Leave blank - this rule alerts when a host fails to respond to ping';
+            break;
+        default:
+            label.textContent = 'Threshold';
+            help.textContent = 'Numeric value that triggers the alert (select a rule type for specific guidance)';
+    }
+}
+
+function saveRule() {
+    const name = document.getElementById('rule-name').value;
+    const ruleType = document.getElementById('rule-type').value;
+    const severity = document.getElementById('rule-severity').value;
+    const threshold = document.getElementById('rule-threshold').value;
+    const configId = document.getElementById('rule-config').value;
+    const emailEnabled = document.getElementById('rule-email').checked;
+    const webhookEnabled = document.getElementById('rule-webhook').checked;
+    const enabled = document.getElementById('rule-enabled').checked;
+
+    if (!name || !ruleType) {
+        alert('Please fill in required fields');
+        return;
+    }
+
+    const data = {
+        name: name,
+        rule_type: ruleType,
+        severity: severity,
+        threshold: threshold ? parseInt(threshold) : null,
+        config_id: configId ? parseInt(configId) : null,
+        email_enabled: emailEnabled,
+        webhook_enabled: webhookEnabled,
+        enabled: enabled
+    };
+
+    // Show spinner
+    document.getElementById('save-rule-text').style.display = 'none';
+    document.getElementById('save-rule-spinner').style.display = 'inline-block';
+
+    const url = editingRuleId
+        ? `/api/alerts/rules/${editingRuleId}`
+        : '/api/alerts/rules';
+    const method = editingRuleId ? 'PUT' : 'POST';
+
+    fetch(url, {
+        method: method,
+        headers: {
+            'Content-Type': 'application/json',
+            'X-API-Key': localStorage.getItem('api_key') || ''
+        },
+        body: JSON.stringify(data)
+    })
+    .then(response => response.json())
+    .then(data => {
+        if (data.status === 'success') {
+            location.reload();
+        } else {
+            alert('Failed to save rule: ' + (data.message || 'Unknown error'));
+            // Hide spinner
+            document.getElementById('save-rule-text').style.display = 'inline';
+            document.getElementById('save-rule-spinner').style.display = 'none';
+        }
+    })
+    .catch(error => {
+        console.error('Error:', error);
+        alert('Failed to save rule');
+        // Hide spinner
+        document.getElementById('save-rule-text').style.display = 'inline';
+        document.getElementById('save-rule-spinner').style.display = 'none';
+    });
+}
+
+function toggleRule(ruleId, enabled) {
+    fetch(`/api/alerts/rules/${ruleId}`, {
+        method: 'PUT',
+        headers: {
+            'Content-Type': 'application/json',
+            'X-API-Key': localStorage.getItem('api_key') || ''
+        },
+        body: JSON.stringify({ enabled: enabled })
+    })
+    .then(response => response.json())
+    .then(data => {
+        if (data.status !== 'success') {
+            alert('Failed to update rule status');
+            // Revert checkbox
+            document.getElementById(`rule-enabled-${ruleId}`).checked = !enabled;
+        } else {
+            // Update label
+            const label = document.querySelector(`label[for="rule-enabled-${ruleId}"] span`);
+            if (enabled) {
+                label.className = 'text-success';
+                label.textContent = 'Active';
+            } else {
+                label.className = 'text-muted';
+                label.textContent = 'Inactive';
+            }
+        }
+    })
+    .catch(error => {
+        console.error('Error:', error);
+        alert('Failed to update rule status');
+        // Revert checkbox
+        document.getElementById(`rule-enabled-${ruleId}`).checked = !enabled;
+    });
+}
+
+function deleteRule(ruleId, ruleName) {
+    if (!confirm(`Delete alert rule "${ruleName}"? This cannot be undone.`)) {
+        return;
+    }
+
+    fetch(`/api/alerts/rules/${ruleId}`, {
+        method: 'DELETE',
+        headers: {
+            'X-API-Key': localStorage.getItem('api_key') || ''
+        }
+    })
+    .then(response => response.json())
+    .then(data => {
+        if (data.status === 'success') {
+            location.reload();
+        } else {
+            alert('Failed to delete rule: ' + (data.message || 'Unknown error'));
+        }
+    })
+    .catch(error => {
+        console.error('Error:', error);
+        alert('Failed to delete rule');
+    });
+}
+</script>
+{% endblock %}

app/web/templates/alerts.html

@@ -0,0 +1,303 @@
+{% extends "base.html" %}
+
+{% block title %}Alerts - SneakyScanner{% endblock %}
+
+{% block content %}
+<div class="row mt-4">
+    <div class="col-12 d-flex justify-content-between align-items-center mb-4">
+        <h1>Alert History</h1>
+        <div>
+            <button class="btn btn-success me-2" onclick="acknowledgeAllAlerts()">
+                <i class="bi bi-check-all"></i> Ack All
+            </button>
+            <a href="{{ url_for('main.alert_rules') }}" class="btn btn-primary">
+                <i class="bi bi-gear"></i> Manage Alert Rules
+            </a>
+        </div>
+    </div>
+</div>
+
+<!-- Alert Statistics -->
+<div class="row mb-4">
+    <div class="col-md-3 mb-3">
+        <div class="card">
+            <div class="card-body">
+                <h6 class="text-muted mb-2">Total Alerts</h6>
+                <h3 class="mb-0">{{ pagination.total }}</h3>
+            </div>
+        </div>
+    </div>
+    <div class="col-md-3 mb-3">
+        <div class="card">
+            <div class="card-body">
+                <h6 class="text-muted mb-2">Critical</h6>
+                <h3 class="mb-0 text-danger">
+                    {{ alerts | selectattr('severity', 'equalto', 'critical') | list | length }}
+                </h3>
+            </div>
+        </div>
+    </div>
+    <div class="col-md-3 mb-3">
+        <div class="card">
+            <div class="card-body">
+                <h6 class="text-muted mb-2">Warnings</h6>
+                <h3 class="mb-0 text-warning">
+                    {{ alerts | selectattr('severity', 'equalto', 'warning') | list | length }}
+                </h3>
+            </div>
+        </div>
+    </div>
+    <div class="col-md-3 mb-3">
+        <div class="card">
+            <div class="card-body">
+                <h6 class="text-muted mb-2">Unacknowledged</h6>
+                <h3 class="mb-0 text-warning">
+                    {{ alerts | rejectattr('acknowledged') | list | length }}
+                </h3>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Filters -->
+<div class="row mb-4">
+    <div class="col-12">
+        <div class="card">
+            <div class="card-body">
+                <form method="get" action="{{ url_for('main.alerts') }}" class="row g-3">
+                    <div class="col-md-3">
+                        <label for="severity-filter" class="form-label">Severity</label>
+                        <select class="form-select" id="severity-filter" name="severity">
+                            <option value="">All Severities</option>
+                            <option value="critical" {% if current_severity == 'critical' %}selected{% endif %}>Critical</option>
+                            <option value="warning" {% if current_severity == 'warning' %}selected{% endif %}>Warning</option>
+                            <option value="info" {% if current_severity == 'info' %}selected{% endif %}>Info</option>
+                        </select>
+                    </div>
+                    <div class="col-md-3">
+                        <label for="type-filter" class="form-label">Alert Type</label>
+                        <select class="form-select" id="type-filter" name="alert_type">
+                            <option value="">All Types</option>
+                            {% for at in alert_types %}
+                            <option value="{{ at }}" {% if current_alert_type == at %}selected{% endif %}>
+                                {{ at.replace('_', ' ').title() }}
+                            </option>
+                            {% endfor %}
+                        </select>
+                    </div>
+                    <div class="col-md-3">
+                        <label for="ack-filter" class="form-label">Acknowledgment</label>
+                        <select class="form-select" id="ack-filter" name="acknowledged">
+                            <option value="">All</option>
+                            <option value="false" {% if current_acknowledged == 'false' %}selected{% endif %}>Unacknowledged</option>
+                            <option value="true" {% if current_acknowledged == 'true' %}selected{% endif %}>Acknowledged</option>
+                        </select>
+                    </div>
+                    <div class="col-md-3 d-flex align-items-end">
+                        <button type="submit" class="btn btn-primary w-100">
+                            <i class="bi bi-funnel"></i> Apply Filters
+                        </button>
+                    </div>
+                </form>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Alerts Table -->
+<div class="row">
+    <div class="col-12">
+        <div class="card">
+            <div class="card-header">
+                <h5 class="mb-0">Alerts</h5>
+            </div>
+            <div class="card-body">
+                {% if alerts %}
+                <div class="table-responsive">
+                    <table class="table table-hover">
+                        <thead>
+                            <tr>
+                                <th style="width: 100px;">Severity</th>
+                                <th>Type</th>
+                                <th>Message</th>
+                                <th style="width: 120px;">Target</th>
+                                <th style="width: 150px;">Scan</th>
+                                <th style="width: 150px;">Created</th>
+                                <th style="width: 100px;">Status</th>
+                                <th style="width: 100px;">Actions</th>
+                            </tr>
+                        </thead>
+                        <tbody>
+                            {% for alert in alerts %}
+                            <tr>
+                                <td>
+                                    {% if alert.severity == 'critical' %}
+                                    <span class="badge bg-danger">Critical</span>
+                                    {% elif alert.severity == 'warning' %}
+                                    <span class="badge bg-warning">Warning</span>
+                                    {% else %}
+                                    <span class="badge bg-info">Info</span>
+                                    {% endif %}
+                                </td>
+                                <td>
+                                    <span class="text-muted">{{ alert.alert_type.replace('_', ' ').title() }}</span>
+                                </td>
+                                <td>
+                                    {{ alert.message }}
+                                </td>
+                                <td>
+                                    {% if alert.ip_address %}
+                                        <small class="text-muted">
+                                            {{ alert.ip_address }}{% if alert.port %}:{{ alert.port }}{% endif %}
+                                        </small>
+                                    {% else %}
+                                        <small class="text-muted">-</small>
+                                    {% endif %}
+                                </td>
+                                <td>
+                                    <a href="{{ url_for('main.scan_detail', scan_id=alert.scan_id) }}" class="text-decoration-none">
+                                        Scan #{{ alert.scan_id }}
+                                    </a>
+                                </td>
+                                <td>
+                                    <small class="text-muted">{{ alert.created_at.strftime('%Y-%m-%d %H:%M') }}</small>
+                                </td>
+                                <td>
+                                    {% if alert.acknowledged %}
+                                    <span class="badge bg-success">
+                                        <i class="bi bi-check-circle"></i> Ack'd
+                                    </span>
+                                    {% else %}
+                                    <span class="badge bg-secondary">New</span>
+                                    {% endif %}
+                                    {% if alert.email_sent %}
+                                    <i class="bi bi-envelope-fill text-muted" title="Email sent"></i>
+                                    {% endif %}
+                                    {% if alert.webhook_sent %}
+                                    <i class="bi bi-send-fill text-muted" title="Webhook sent"></i>
+                                    {% endif %}
+                                </td>
+                                <td>
+                                    {% if not alert.acknowledged %}
+                                    <button class="btn btn-sm btn-outline-success" onclick="acknowledgeAlert({{ alert.id }})">
+                                        <i class="bi bi-check"></i> Ack
+                                    </button>
+                                    {% else %}
+                                    <small class="text-muted" title="Acknowledged by {{ alert.acknowledged_by }} at {{ alert.acknowledged_at.strftime('%Y-%m-%d %H:%M') }}">
+                                        By: {{ alert.acknowledged_by }}
+                                    </small>
+                                    {% endif %}
+                                </td>
+                            </tr>
+                            {% endfor %}
+                        </tbody>
+                    </table>
+                </div>
+
+                <!-- Pagination -->
+                {% if pagination.pages > 1 %}
+                <nav aria-label="Alert pagination" class="mt-4">
+                    <ul class="pagination justify-content-center">
+                        <li class="page-item {% if not pagination.has_prev %}disabled{% endif %}">
+                            <a class="page-link" href="{{ url_for('main.alerts', page=pagination.prev_num, severity=current_severity, alert_type=current_alert_type, acknowledged=current_acknowledged) }}">
+                                Previous
+                            </a>
+                        </li>
+
+                        {% for page_num in pagination.iter_pages(left_edge=1, left_current=1, right_current=2, right_edge=1) %}
+                            {% if page_num %}
+                                <li class="page-item {% if page_num == pagination.page %}active{% endif %}">
+                                    <a class="page-link" href="{{ url_for('main.alerts', page=page_num, severity=current_severity, alert_type=current_alert_type, acknowledged=current_acknowledged) }}">
+                                        {{ page_num }}
+                                    </a>
+                                </li>
+                            {% else %}
+                                <li class="page-item disabled">
+                                    <span class="page-link">...</span>
+                                </li>
+                            {% endif %}
+                        {% endfor %}
+
+                        <li class="page-item {% if not pagination.has_next %}disabled{% endif %}">
+                            <a class="page-link" href="{{ url_for('main.alerts', page=pagination.next_num, severity=current_severity, alert_type=current_alert_type, acknowledged=current_acknowledged) }}">
+                                Next
+                            </a>
+                        </li>
+                    </ul>
+                </nav>
+                {% endif %}
+                {% else %}
+                <div class="text-center py-5 text-muted">
+                    <i class="bi bi-bell-slash" style="font-size: 3rem;"></i>
+                    <h5 class="mt-3">No alerts found</h5>
+                    <p>Alerts will appear here when scan results trigger alert rules.</p>
+                    <a href="{{ url_for('main.alert_rules') }}" class="btn btn-primary mt-3">
+                        <i class="bi bi-plus-circle"></i> Configure Alert Rules
+                    </a>
+                </div>
+                {% endif %}
+            </div>
+        </div>
+    </div>
+</div>
+
+<script>
+function acknowledgeAlert(alertId) {
+    if (!confirm('Acknowledge this alert?')) {
+        return;
+    }
+
+    fetch(`/api/alerts/${alertId}/acknowledge`, {
+        method: 'POST',
+        headers: {
+            'Content-Type': 'application/json',
+            'X-API-Key': localStorage.getItem('api_key') || ''
+        },
+        body: JSON.stringify({
+            acknowledged_by: 'web_user'
+        })
+    })
+    .then(response => response.json())
+    .then(data => {
+        if (data.status === 'success') {
+            location.reload();
+        } else {
+            alert('Failed to acknowledge alert: ' + (data.message || 'Unknown error'));
+        }
+    })
+    .catch(error => {
+        console.error('Error:', error);
+        alert('Failed to acknowledge alert');
+    });
+}
+
+function acknowledgeAllAlerts() {
+    if (!confirm('Acknowledge all unacknowledged alerts?')) {
+        return;
+    }
+
+    fetch('/api/alerts/acknowledge-all', {
+        method: 'POST',
+        headers: {
+            'Content-Type': 'application/json',
+            'X-API-Key': localStorage.getItem('api_key') || ''
+        },
+        body: JSON.stringify({
+            acknowledged_by: 'web_user'
+        })
+    })
+    .then(response => response.json())
+    .then(data => {
+        if (data.status === 'success') {
+            location.reload();
+        } else {
+            alert('Failed to acknowledge alerts: ' + (data.message || 'Unknown error'));
+        }
+    })
+    .catch(error => {
+        console.error('Error:', error);
+        alert('Failed to acknowledge alerts');
+    });
+}
+</script>
+{% endblock %}

app/web/templates/base.html

@@ -3,7 +3,7 @@
 <head>
     <meta charset="UTF-8">
     <meta name="viewport" content="width=device-width, initial-scale=1.0">
-    <title>{% block title %}SneakyScanner{% endblock %}</title>
+    <title>{% block title %}{{ app_name }}{% endblock %}</title>
 
     <!-- Bootstrap 5 CSS -->
     <link href="https://cdn.jsdelivr.net/npm/bootstrap@5.3.0/dist/css/bootstrap.min.css" rel="stylesheet">
@@ -34,7 +34,7 @@
     <nav class="navbar navbar-expand-lg navbar-custom">
         <div class="container-fluid">
             <a class="navbar-brand" href="{{ url_for('main.dashboard') }}">
-                SneakyScanner
+                {{ app_name }}
             </a>
             <button class="navbar-toggler" type="button" data-bs-toggle="collapse" data-bs-target="#navbarNav">
                 <span class="navbar-toggler-icon"></span>
@@ -45,6 +45,16 @@
                         <a class="nav-link {% if request.endpoint == 'main.dashboard' %}active{% endif %}"
                            href="{{ url_for('main.dashboard') }}">Dashboard</a>
                     </li>
+                    <li class="nav-item dropdown">
+                        <a class="nav-link dropdown-toggle {% if request.endpoint and ('config' in request.endpoint or request.endpoint == 'main.sites') %}active{% endif %}"
+                           href="#" id="configsDropdown" role="button" data-bs-toggle="dropdown">
+                            Configs
+                        </a>
+                        <ul class="dropdown-menu" aria-labelledby="configsDropdown">
+                            <li><a class="dropdown-item" href="{{ url_for('main.configs') }}">Scan Configs</a></li>
+                            <li><a class="dropdown-item" href="{{ url_for('main.sites') }}">Sites</a></li>
+                        </ul>
+                    </li>
                     <li class="nav-item">
                         <a class="nav-link {% if request.endpoint == 'main.scans' %}active{% endif %}"
                            href="{{ url_for('main.scans') }}">Scans</a>
@@ -53,8 +63,33 @@
                         <a class="nav-link {% if request.endpoint and 'schedule' in request.endpoint %}active{% endif %}"
                            href="{{ url_for('main.schedules') }}">Schedules</a>
                     </li>
+                    <li class="nav-item dropdown">
+                        <a class="nav-link dropdown-toggle {% if request.endpoint and ('alert' in request.endpoint or 'webhook' in request.endpoint) %}active{% endif %}"
+                           href="#" id="alertsDropdown" role="button" data-bs-toggle="dropdown">
+                            Alerts
+                        </a>
+                        <ul class="dropdown-menu" aria-labelledby="alertsDropdown">
+                            <li><a class="dropdown-item" href="{{ url_for('main.alerts') }}">Alert History</a></li>
+                            <li><a class="dropdown-item" href="{{ url_for('main.alert_rules') }}">Alert Rules</a></li>
+                            <li><hr class="dropdown-divider"></li>
+                            <li><a class="dropdown-item" href="{{ url_for('webhooks.list_webhooks') }}">Webhooks</a></li>
                         </ul>
+                    </li>
+                </ul>
+                <form class="d-flex me-3" action="{{ url_for('main.search_ip') }}" method="GET">
+                    <input class="form-control form-control-sm me-2" type="search" name="ip"
+                           placeholder="Search IP..." aria-label="Search IP" style="width: 150px;">
+                    <button class="btn btn-outline-primary btn-sm" type="submit">
+                        <i class="bi bi-search"></i>
+                    </button>
+                </form>
                 <ul class="navbar-nav">
+                    <li class="nav-item">
+                        <a class="nav-link {% if request.endpoint == 'main.help' %}active{% endif %}"
+                           href="{{ url_for('main.help') }}">
+                            <i class="bi bi-question-circle"></i> Help
+                        </a>
+                    </li>
                     <li class="nav-item">
                         <a class="nav-link" href="{{ url_for('auth.logout') }}">Logout</a>
                     </li>
@@ -81,10 +116,13 @@
 
     <div class="footer">
         <div class="container-fluid">
-            SneakyScanner v1.0 - Phase 3 In Progress
+            <a href="{{ repo_url }}" target="_blank">{{ app_name }}</a> - v{{ app_version }}
         </div>
     </div>
 
+    <!-- Global notification container - always above modals -->
+    <div id="notification-container" style="position: fixed; top: 20px; right: 20px; z-index: 9999; min-width: 300px;"></div>
+
     <script src="https://cdn.jsdelivr.net/npm/bootstrap@5.3.0/dist/js/bootstrap.bundle.min.js"></script>
     {% block scripts %}{% endblock %}
 </body>

app/web/templates/configs.html

@@ -0,0 +1,580 @@
+{% extends "base.html" %}
+
+{% block title %}Scan Configurations - SneakyScanner{% endblock %}
+
+{% block content %}
+<div class="row mt-4">
+    <div class="col-12">
+        <div class="d-flex justify-content-between align-items-center mb-4">
+            <h1>Scan Configurations</h1>
+            <div>
+                <button class="btn btn-primary" data-bs-toggle="modal" data-bs-target="#createConfigModal">
+                    <i class="bi bi-plus-circle"></i> Create New Config
+                </button>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Summary Stats -->
+<div class="row mb-4">
+    <div class="col-md-4">
+        <div class="stat-card">
+            <div class="stat-value" id="total-configs">-</div>
+            <div class="stat-label">Total Configs</div>
+        </div>
+    </div>
+    <div class="col-md-4">
+        <div class="stat-card">
+            <div class="stat-value" id="total-sites-used">-</div>
+            <div class="stat-label">Total Sites Referenced</div>
+        </div>
+    </div>
+    <div class="col-md-4">
+        <div class="stat-card">
+            <div class="stat-value" id="recent-updates">-</div>
+            <div class="stat-label">Updated This Week</div>
+        </div>
+    </div>
+</div>
+
+<!-- Configs Table -->
+<div class="row">
+    <div class="col-12">
+        <div class="card">
+            <div class="card-header">
+                <div class="d-flex justify-content-between align-items-center">
+                    <h5 class="mb-0">All Configurations</h5>
+                    <input type="text" id="search-input" class="form-control" style="max-width: 300px;"
+                           placeholder="Search configs...">
+                </div>
+            </div>
+            <div class="card-body">
+                <div id="configs-loading" class="text-center py-5">
+                    <div class="spinner-border text-primary" role="status">
+                        <span class="visually-hidden">Loading...</span>
+                    </div>
+                    <p class="mt-3 text-muted">Loading configurations...</p>
+                </div>
+                <div id="configs-error" style="display: none;" class="alert alert-danger">
+                    <strong>Error:</strong> <span id="error-message"></span>
+                </div>
+                <div id="configs-content" style="display: none;">
+                    <div class="table-responsive">
+                        <table class="table table-hover">
+                            <thead>
+                                <tr>
+                                    <th>Title</th>
+                                    <th>Description</th>
+                                    <th>Sites</th>
+                                    <th>Updated</th>
+                                    <th>Actions</th>
+                                </tr>
+                            </thead>
+                            <tbody id="configs-tbody">
+                                <!-- Populated by JavaScript -->
+                            </tbody>
+                        </table>
+                    </div>
+                    <div id="empty-state" style="display: none;" class="text-center py-5">
+                        <i class="bi bi-gear" style="font-size: 3rem; color: #64748b;"></i>
+                        <h5 class="mt-3 text-muted">No configurations defined</h5>
+                        <p class="text-muted">Create your first scan configuration</p>
+                        <button class="btn btn-primary mt-2" data-bs-toggle="modal" data-bs-target="#createConfigModal">
+                            <i class="bi bi-plus-circle"></i> Create Config
+                        </button>
+                    </div>
+                </div>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Create Config Modal -->
+<div class="modal fade" id="createConfigModal" tabindex="-1">
+    <div class="modal-dialog modal-lg">
+        <div class="modal-content">
+            <div class="modal-header">
+                <h5 class="modal-title">
+                    <i class="bi bi-plus-circle me-2"></i>Create New Configuration
+                </h5>
+                <button type="button" class="btn-close" data-bs-dismiss="modal"></button>
+            </div>
+            <div class="modal-body">
+                <form id="create-config-form">
+                    <div class="mb-3">
+                        <label for="config-title" class="form-label">Title <span class="text-danger">*</span></label>
+                        <input type="text" class="form-control" id="config-title" required
+                               placeholder="e.g., Production Weekly Scan">
+                    </div>
+
+                    <div class="mb-3">
+                        <label for="config-description" class="form-label">Description</label>
+                        <textarea class="form-control" id="config-description" rows="3"
+                                  placeholder="Optional description of this configuration"></textarea>
+                    </div>
+
+                    <div class="mb-3">
+                        <label class="form-label">Sites <span class="text-danger">*</span></label>
+                        <div id="sites-loading-modal" class="text-center py-3">
+                            <div class="spinner-border spinner-border-sm text-primary" role="status">
+                                <span class="visually-hidden">Loading...</span>
+                            </div>
+                            <span class="ms-2 text-muted">Loading available sites...</span>
+                        </div>
+                        <div id="sites-list" style="display: none;">
+                            <!-- Populated by JavaScript -->
+                        </div>
+                        <small class="form-text text-muted">Select at least one site to include in this configuration</small>
+                    </div>
+
+                    <div class="alert alert-danger" id="create-config-error" style="display: none;">
+                        <span id="create-config-error-message"></span>
+                    </div>
+                </form>
+            </div>
+            <div class="modal-footer">
+                <button type="button" class="btn btn-secondary" data-bs-dismiss="modal">Cancel</button>
+                <button type="button" class="btn btn-primary" id="create-config-btn">
+                    <i class="bi bi-check-circle me-1"></i>Create Configuration
+                </button>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Edit Config Modal -->
+<div class="modal fade" id="editConfigModal" tabindex="-1">
+    <div class="modal-dialog modal-lg">
+        <div class="modal-content">
+            <div class="modal-header">
+                <h5 class="modal-title">
+                    <i class="bi bi-pencil me-2"></i>Edit Configuration
+                </h5>
+                <button type="button" class="btn-close" data-bs-dismiss="modal"></button>
+            </div>
+            <div class="modal-body">
+                <form id="edit-config-form">
+                    <input type="hidden" id="edit-config-id">
+
+                    <div class="mb-3">
+                        <label for="edit-config-title" class="form-label">Title <span class="text-danger">*</span></label>
+                        <input type="text" class="form-control" id="edit-config-title" required>
+                    </div>
+
+                    <div class="mb-3">
+                        <label for="edit-config-description" class="form-label">Description</label>
+                        <textarea class="form-control" id="edit-config-description" rows="3"></textarea>
+                    </div>
+
+                    <div class="mb-3">
+                        <label class="form-label">Sites <span class="text-danger">*</span></label>
+                        <div id="edit-sites-list">
+                            <!-- Populated by JavaScript -->
+                        </div>
+                    </div>
+
+                    <div class="alert alert-danger" id="edit-config-error" style="display: none;">
+                        <span id="edit-config-error-message"></span>
+                    </div>
+                </form>
+            </div>
+            <div class="modal-footer">
+                <button type="button" class="btn btn-secondary" data-bs-dismiss="modal">Cancel</button>
+                <button type="button" class="btn btn-primary" id="edit-config-btn">
+                    <i class="bi bi-check-circle me-1"></i>Save Changes
+                </button>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- View Config Modal -->
+<div class="modal fade" id="viewConfigModal" tabindex="-1">
+    <div class="modal-dialog modal-lg">
+        <div class="modal-content">
+            <div class="modal-header">
+                <h5 class="modal-title">
+                    <i class="bi bi-eye me-2"></i>Configuration Details
+                </h5>
+                <button type="button" class="btn-close" data-bs-dismiss="modal"></button>
+            </div>
+            <div class="modal-body">
+                <div id="view-config-content">
+                    <!-- Populated by JavaScript -->
+                </div>
+            </div>
+            <div class="modal-footer">
+                <button type="button" class="btn btn-secondary" data-bs-dismiss="modal">Close</button>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Delete Confirmation Modal -->
+<div class="modal fade" id="deleteConfigModal" tabindex="-1">
+    <div class="modal-dialog">
+        <div class="modal-content">
+            <div class="modal-header">
+                <h5 class="modal-title text-danger">
+                    <i class="bi bi-trash me-2"></i>Delete Configuration
+                </h5>
+                <button type="button" class="btn-close" data-bs-dismiss="modal"></button>
+            </div>
+            <div class="modal-body">
+                <p>Are you sure you want to delete configuration <strong id="delete-config-name"></strong>?</p>
+                <p class="text-warning"><i class="bi bi-exclamation-triangle"></i> This action cannot be undone.</p>
+                <input type="hidden" id="delete-config-id">
+            </div>
+            <div class="modal-footer">
+                <button type="button" class="btn btn-secondary" data-bs-dismiss="modal">Cancel</button>
+                <button type="button" class="btn btn-danger" id="confirm-delete-btn">
+                    <i class="bi bi-trash me-1"></i>Delete
+                </button>
+            </div>
+        </div>
+    </div>
+</div>
+
+{% endblock %}
+
+{% block scripts %}
+<script>
+// Global state
+let allConfigs = [];
+let allSites = [];
+
+// Load data on page load
+document.addEventListener('DOMContentLoaded', function() {
+    loadSites();
+    loadConfigs();
+});
+
+// Load all sites
+async function loadSites() {
+    try {
+        const response = await fetch('/api/sites?all=true');
+        if (!response.ok) throw new Error('Failed to load sites');
+
+        const data = await response.json();
+        allSites = data.sites || [];
+
+        renderSitesCheckboxes();
+    } catch (error) {
+        console.error('Error loading sites:', error);
+        document.getElementById('sites-loading-modal').innerHTML =
+            '<div class="alert alert-danger">Failed to load sites</div>';
+    }
+}
+
+// Render sites checkboxes
+function renderSitesCheckboxes(selectedIds = [], isEditMode = false) {
+    const container = isEditMode ? document.getElementById('edit-sites-list') : document.getElementById('sites-list');
+
+    if (!container) return;
+
+    if (allSites.length === 0) {
+        const message = '<div class="alert alert-info">No sites available. <a href="/sites">Create a site first</a>.</div>';
+        container.innerHTML = message;
+        if (!isEditMode) {
+            document.getElementById('sites-loading-modal').style.display = 'none';
+            container.style.display = 'block';
+        }
+        return;
+    }
+
+    const prefix = isEditMode ? 'edit-site' : 'site';
+    const checkboxClass = isEditMode ? 'edit-site-checkbox' : 'site-checkbox';
+
+    let html = '<div style="max-height: 300px; overflow-y: auto;">';
+    allSites.forEach(site => {
+        const isChecked = selectedIds.includes(site.id);
+        html += `
+            <div class="form-check">
+                <input class="form-check-input ${checkboxClass}" type="checkbox" value="${site.id}"
+                       id="${prefix}-${site.id}" ${isChecked ? 'checked' : ''}>
+                <label class="form-check-label" for="${prefix}-${site.id}">
+                    ${escapeHtml(site.name)}
+                    <small class="text-muted">(${site.ip_count || 0} IP${site.ip_count !== 1 ? 's' : ''})</small>
+                </label>
+            </div>
+        `;
+    });
+    html += '</div>';
+
+    container.innerHTML = html;
+
+    if (!isEditMode) {
+        document.getElementById('sites-loading-modal').style.display = 'none';
+        container.style.display = 'block';
+    }
+}
+
+// Load all configs
+async function loadConfigs() {
+    try {
+        const response = await fetch('/api/configs');
+        if (!response.ok) throw new Error('Failed to load configs');
+
+        const data = await response.json();
+        allConfigs = data.configs || [];
+
+        renderConfigs();
+        updateStats();
+
+        document.getElementById('configs-loading').style.display = 'none';
+        document.getElementById('configs-content').style.display = 'block';
+    } catch (error) {
+        console.error('Error loading configs:', error);
+        document.getElementById('configs-loading').style.display = 'none';
+        document.getElementById('configs-error').style.display = 'block';
+        document.getElementById('error-message').textContent = error.message;
+    }
+}
+
+// Render configs table
+function renderConfigs(filter = '') {
+    const tbody = document.getElementById('configs-tbody');
+    const emptyState = document.getElementById('empty-state');
+
+    const filteredConfigs = filter
+        ? allConfigs.filter(c =>
+            c.title.toLowerCase().includes(filter.toLowerCase()) ||
+            (c.description && c.description.toLowerCase().includes(filter.toLowerCase()))
+          )
+        : allConfigs;
+
+    if (filteredConfigs.length === 0) {
+        tbody.innerHTML = '';
+        emptyState.style.display = 'block';
+        return;
+    }
+
+    emptyState.style.display = 'none';
+    tbody.innerHTML = filteredConfigs.map(config => `
+        <tr>
+            <td><strong>${escapeHtml(config.title)}</strong></td>
+            <td>${config.description ? escapeHtml(config.description) : '<span class="text-muted">-</span>'}</td>
+            <td>
+                <span class="badge bg-primary">${config.site_count} site${config.site_count !== 1 ? 's' : ''}</span>
+            </td>
+            <td>${formatDate(config.updated_at)}</td>
+            <td>
+                <button class="btn btn-sm btn-info" onclick="viewConfig(${config.id})" title="View">
+                    <i class="bi bi-eye"></i>
+                </button>
+                <button class="btn btn-sm btn-warning" onclick="editConfig(${config.id})" title="Edit">
+                    <i class="bi bi-pencil"></i>
+                </button>
+                <button class="btn btn-sm btn-danger" onclick="deleteConfig(${config.id}, '${escapeHtml(config.title).replace(/'/g, "\\'")}');" title="Delete">
+                    <i class="bi bi-trash"></i>
+                </button>
+            </td>
+        </tr>
+    `).join('');
+}
+
+// Update stats
+function updateStats() {
+    document.getElementById('total-configs').textContent = allConfigs.length;
+
+    const uniqueSites = new Set();
+    allConfigs.forEach(c => c.sites.forEach(s => uniqueSites.add(s.id)));
+    document.getElementById('total-sites-used').textContent = uniqueSites.size;
+
+    const oneWeekAgo = new Date();
+    oneWeekAgo.setDate(oneWeekAgo.getDate() - 7);
+    const recentUpdates = allConfigs.filter(c => new Date(c.updated_at) > oneWeekAgo).length;
+    document.getElementById('recent-updates').textContent = recentUpdates;
+}
+
+// Search functionality
+document.getElementById('search-input').addEventListener('input', function(e) {
+    renderConfigs(e.target.value);
+});
+
+// Create config
+document.getElementById('create-config-btn').addEventListener('click', async function() {
+    const title = document.getElementById('config-title').value.trim();
+    const description = document.getElementById('config-description').value.trim();
+    const siteCheckboxes = document.querySelectorAll('.site-checkbox:checked');
+    const siteIds = Array.from(siteCheckboxes).map(cb => parseInt(cb.value));
+
+    if (!title) {
+        showError('create-config-error', 'Title is required');
+        return;
+    }
+
+    if (siteIds.length === 0) {
+        showError('create-config-error', 'At least one site must be selected');
+        return;
+    }
+
+    try {
+        const response = await fetch('/api/configs', {
+            method: 'POST',
+            headers: { 'Content-Type': 'application/json' },
+            body: JSON.stringify({ title, description: description || null, site_ids: siteIds })
+        });
+
+        if (!response.ok) {
+            const data = await response.json();
+            throw new Error(data.message || 'Failed to create config');
+        }
+
+        // Close modal and reload
+        bootstrap.Modal.getInstance(document.getElementById('createConfigModal')).hide();
+        document.getElementById('create-config-form').reset();
+        renderSitesCheckboxes(); // Reset checkboxes
+        await loadConfigs();
+    } catch (error) {
+        showError('create-config-error', error.message);
+    }
+});
+
+// View config
+async function viewConfig(id) {
+    try {
+        const response = await fetch(`/api/configs/${id}`);
+        if (!response.ok) throw new Error('Failed to load config');
+
+        const config = await response.json();
+
+        let html = `
+            <div class="mb-3">
+                <strong>Title:</strong> ${escapeHtml(config.title)}
+            </div>
+            <div class="mb-3">
+                <strong>Description:</strong> ${config.description ? escapeHtml(config.description) : '<span class="text-muted">None</span>'}
+            </div>
+            <div class="mb-3">
+                <strong>Sites (${config.site_count}):</strong>
+                <ul class="mt-2">
+                    ${config.sites.map(site => `
+                        <li>${escapeHtml(site.name)} <small class="text-muted">(${site.ip_count} IP${site.ip_count !== 1 ? 's' : ''})</small></li>
+                    `).join('')}
+                </ul>
+            </div>
+            <div class="mb-3">
+                <strong>Created:</strong> ${formatDate(config.created_at)}
+            </div>
+            <div class="mb-3">
+                <strong>Last Updated:</strong> ${formatDate(config.updated_at)}
+            </div>
+        `;
+
+        document.getElementById('view-config-content').innerHTML = html;
+        new bootstrap.Modal(document.getElementById('viewConfigModal')).show();
+    } catch (error) {
+        alert('Error loading config: ' + error.message);
+    }
+}
+
+// Edit config
+async function editConfig(id) {
+    try {
+        const response = await fetch(`/api/configs/${id}`);
+        if (!response.ok) throw new Error('Failed to load config');
+
+        const config = await response.json();
+
+        document.getElementById('edit-config-id').value = config.id;
+        document.getElementById('edit-config-title').value = config.title;
+        document.getElementById('edit-config-description').value = config.description || '';
+
+        const selectedIds = config.sites.map(s => s.id);
+        renderSitesCheckboxes(selectedIds, true);  // true = isEditMode
+
+        new bootstrap.Modal(document.getElementById('editConfigModal')).show();
+    } catch (error) {
+        alert('Error loading config: ' + error.message);
+    }
+}
+
+// Save edited config
+document.getElementById('edit-config-btn').addEventListener('click', async function() {
+    const id = document.getElementById('edit-config-id').value;
+    const title = document.getElementById('edit-config-title').value.trim();
+    const description = document.getElementById('edit-config-description').value.trim();
+    const siteCheckboxes = document.querySelectorAll('.edit-site-checkbox:checked');
+    const siteIds = Array.from(siteCheckboxes).map(cb => parseInt(cb.value));
+
+    if (!title) {
+        showError('edit-config-error', 'Title is required');
+        return;
+    }
+
+    if (siteIds.length === 0) {
+        showError('edit-config-error', 'At least one site must be selected');
+        return;
+    }
+
+    try {
+        const response = await fetch(`/api/configs/${id}`, {
+            method: 'PUT',
+            headers: { 'Content-Type': 'application/json' },
+            body: JSON.stringify({ title, description: description || null, site_ids: siteIds })
+        });
+
+        if (!response.ok) {
+            const data = await response.json();
+            throw new Error(data.message || 'Failed to update config');
+        }
+
+        // Close modal and reload
+        bootstrap.Modal.getInstance(document.getElementById('editConfigModal')).hide();
+        await loadConfigs();
+    } catch (error) {
+        showError('edit-config-error', error.message);
+    }
+});
+
+// Delete config
+function deleteConfig(id, name) {
+    document.getElementById('delete-config-id').value = id;
+    document.getElementById('delete-config-name').textContent = name;
+    new bootstrap.Modal(document.getElementById('deleteConfigModal')).show();
+}
+
+// Confirm delete
+document.getElementById('confirm-delete-btn').addEventListener('click', async function() {
+    const id = document.getElementById('delete-config-id').value;
+
+    try {
+        const response = await fetch(`/api/configs/${id}`, { method: 'DELETE' });
+
+        if (!response.ok) {
+            const data = await response.json();
+            throw new Error(data.message || 'Failed to delete config');
+        }
+
+        // Close modal and reload
+        bootstrap.Modal.getInstance(document.getElementById('deleteConfigModal')).hide();
+        await loadConfigs();
+    } catch (error) {
+        alert('Error deleting config: ' + error.message);
+    }
+});
+
+// Utility functions
+function showError(elementId, message) {
+    const errorEl = document.getElementById(elementId);
+    const messageEl = document.getElementById(elementId + '-message');
+    messageEl.textContent = message;
+    errorEl.style.display = 'block';
+}
+
+function escapeHtml(text) {
+    if (!text) return '';
+    const div = document.createElement('div');
+    div.textContent = text;
+    return div.innerHTML;
+}
+
+function formatDate(dateStr) {
+    if (!dateStr) return '-';
+    const date = new Date(dateStr);
+    return date.toLocaleDateString() + ' ' + date.toLocaleTimeString();
+}
+</script>
+{% endblock %}

app/web/templates/dashboard.html

@@ -5,7 +5,7 @@
 {% block content %}
 <div class="row mt-4">
     <div class="col-12">
-        <h1 class="mb-4" style="color: #60a5fa;">Dashboard</h1>
+        <h1 class="mb-4">Dashboard</h1>
     </div>
 </div>
 
@@ -42,7 +42,7 @@
     <div class="col-12">
         <div class="card">
             <div class="card-header">
-                <h5 class="mb-0" style="color: #60a5fa;">Quick Actions</h5>
+                <h5 class="mb-0">Quick Actions</h5>
             </div>
             <div class="card-body">
                 <button class="btn btn-primary btn-lg" onclick="showTriggerScanModal()">
@@ -63,7 +63,7 @@
     <div class="col-md-8">
         <div class="card">
             <div class="card-header">
-                <h5 class="mb-0" style="color: #60a5fa;">Scan Activity (Last 30 Days)</h5>
+                <h5 class="mb-0">Scan Activity (Last 30 Days)</h5>
             </div>
             <div class="card-body">
                 <div id="chart-loading" class="text-center py-4">
@@ -80,7 +80,7 @@
     <div class="col-md-4">
         <div class="card h-100">
             <div class="card-header d-flex justify-content-between align-items-center">
-                <h5 class="mb-0" style="color: #60a5fa;">Upcoming Schedules</h5>
+                <h5 class="mb-0">Upcoming Schedules</h5>
                 <a href="{{ url_for('main.schedules') }}" class="btn btn-sm btn-secondary">Manage</a>
             </div>
             <div class="card-body">
@@ -105,7 +105,7 @@
     <div class="col-12">
         <div class="card">
             <div class="card-header d-flex justify-content-between align-items-center">
-                <h5 class="mb-0" style="color: #60a5fa;">Recent Scans</h5>
+                <h5 class="mb-0">Recent Scans</h5>
                 <button class="btn btn-sm btn-secondary" onclick="refreshScans()">
                     <span id="refresh-text">Refresh</span>
                     <span id="refresh-spinner" class="spinner-border spinner-border-sm ms-1" style="display: none;"></span>
@@ -145,35 +145,36 @@
 <!-- Trigger Scan Modal -->
 <div class="modal fade" id="triggerScanModal" tabindex="-1">
     <div class="modal-dialog">
-        <div class="modal-content" style="background-color: #1e293b; border: 1px solid #334155;">
-            <div class="modal-header" style="border-bottom: 1px solid #334155;">
-                <h5 class="modal-title" style="color: #60a5fa;">Trigger New Scan</h5>
+        <div class="modal-content">
+            <div class="modal-header">
+                <h5 class="modal-title">Trigger New Scan</h5>
                 <button type="button" class="btn-close" data-bs-dismiss="modal"></button>
             </div>
             <div class="modal-body">
                 <form id="trigger-scan-form">
                     <div class="mb-3">
-                        <label for="config-file" class="form-label">Config File</label>
-                        <select class="form-select" id="config-file" name="config_file" required>
-                            <option value="">Select a config file...</option>
-                            {% for config in config_files %}
-                            <option value="{{ config }}">{{ config }}</option>
-                            {% endfor %}
+                        <label for="config-select" class="form-label">Scan Configuration</label>
+                        <select class="form-select" id="config-select" name="config_id" required>
+                            <option value="">Loading configurations...</option>
                         </select>
-                        <div class="form-text text-muted">
-                            {% if config_files %}
-                                Select a scan configuration file
-                            {% else %}
-                                <span class="text-warning">No config files found in /app/configs/</span>
-                            {% endif %}
+                        <div class="form-text text-muted" id="config-help-text">
+                            Select a scan configuration
+                        </div>
+                        <div id="no-configs-warning" class="alert alert-warning mt-2 mb-0" role="alert" style="display: none;">
+                            <i class="bi bi-exclamation-triangle"></i>
+                            <strong>No configurations available</strong>
+                            <p class="mb-2 mt-2">You need to create a configuration before you can trigger a scan.</p>
+                            <a href="{{ url_for('main.configs') }}" class="btn btn-sm btn-primary">
+                                <i class="bi bi-plus-circle"></i> Create Configuration
+                            </a>
                         </div>
                     </div>
                     <div id="trigger-error" class="alert alert-danger" style="display: none;"></div>
                 </form>
             </div>
-            <div class="modal-footer" style="border-top: 1px solid #334155;">
+            <div class="modal-footer">
                 <button type="button" class="btn btn-secondary" data-bs-dismiss="modal">Cancel</button>
-                <button type="button" class="btn btn-primary" onclick="triggerScan()">
+                <button type="button" class="btn btn-primary" id="trigger-scan-btn" onclick="triggerScan()">
                     <span id="modal-trigger-text">Trigger Scan</span>
                     <span id="modal-trigger-spinner" class="spinner-border spinner-border-sm ms-2" style="display: none;"></span>
                 </button>
@@ -316,23 +317,75 @@
         });
     }
 
+    // Load available configs
+    async function loadConfigs() {
+        const selectEl = document.getElementById('config-select');
+        const helpTextEl = document.getElementById('config-help-text');
+        const noConfigsWarning = document.getElementById('no-configs-warning');
+        const triggerBtn = document.getElementById('trigger-scan-btn');
+
+        try {
+            const response = await fetch('/api/configs');
+            if (!response.ok) {
+                throw new Error('Failed to load configurations');
+            }
+
+            const data = await response.json();
+            const configs = data.configs || [];
+
+            // Clear existing options
+            selectEl.innerHTML = '';
+
+            if (configs.length === 0) {
+                selectEl.innerHTML = '<option value="">No configurations available</option>';
+                selectEl.disabled = true;
+                triggerBtn.disabled = true;
+                helpTextEl.style.display = 'none';
+                noConfigsWarning.style.display = 'block';
+            } else {
+                selectEl.innerHTML = '<option value="">Select a configuration...</option>';
+                configs.forEach(config => {
+                    const option = document.createElement('option');
+                    option.value = config.id;
+                    const siteText = config.site_count === 1 ? 'site' : 'sites';
+                    option.textContent = `${config.title} (${config.site_count} ${siteText})`;
+                    selectEl.appendChild(option);
+                });
+                selectEl.disabled = false;
+                triggerBtn.disabled = false;
+                helpTextEl.style.display = 'block';
+                noConfigsWarning.style.display = 'none';
+            }
+        } catch (error) {
+            console.error('Error loading configs:', error);
+            selectEl.innerHTML = '<option value="">Error loading configurations</option>';
+            selectEl.disabled = true;
+            triggerBtn.disabled = true;
+            helpTextEl.style.display = 'none';
+        }
+    }
+
     // Show trigger scan modal
     function showTriggerScanModal() {
         const modal = new bootstrap.Modal(document.getElementById('triggerScanModal'));
         document.getElementById('trigger-error').style.display = 'none';
         document.getElementById('trigger-scan-form').reset();
+
+        // Load configs when modal is shown
+        loadConfigs();
+
         modal.show();
     }
 
     // Trigger scan
     async function triggerScan() {
-        const configFile = document.getElementById('config-file').value;
+        const configId = document.getElementById('config-select').value;
         const errorEl = document.getElementById('trigger-error');
         const btnText = document.getElementById('modal-trigger-text');
         const btnSpinner = document.getElementById('modal-trigger-spinner');
 
-        if (!configFile) {
-            errorEl.textContent = 'Please enter a config file path.';
+        if (!configId) {
+            errorEl.textContent = 'Please select a configuration.';
             errorEl.style.display = 'block';
             return;
         }
@@ -349,7 +402,7 @@
                     'Content-Type': 'application/json',
                 },
                 body: JSON.stringify({
-                    config_file: configFile
+                    config_id: parseInt(configId)
                 })
             });
 
@@ -360,6 +413,9 @@
 
             const data = await response.json();
 
+            // Hide error before closing modal to prevent flash
+            errorEl.style.display = 'none';
+
             // Close modal
             bootstrap.Modal.getInstance(document.getElementById('triggerScanModal')).hide();
 
@@ -370,7 +426,9 @@
                 Scan triggered successfully! (ID: ${data.scan_id})
                 <button type="button" class="btn-close" data-bs-dismiss="alert"></button>
             `;
-            document.querySelector('.container-fluid').insertBefore(alertDiv, document.querySelector('.row'));
+            // Insert at the beginning of container-fluid
+            const container = document.querySelector('.container-fluid');
+            container.insertBefore(alertDiv, container.firstChild);
 
             // Refresh scans and stats
             refreshScans();

app/web/templates/help.html

@@ -0,0 +1,375 @@
+{% extends "base.html" %}
+
+{% block title %}Help - SneakyScanner{% endblock %}
+
+{% block content %}
+<div class="row mt-4">
+    <div class="col-12">
+        <h1 class="mb-4"><i class="bi bi-question-circle"></i> Help & Documentation</h1>
+        <p class="text-muted">Learn how to use SneakyScanner to manage your network scanning operations.</p>
+    </div>
+</div>
+
+<!-- Quick Navigation -->
+<div class="row mb-4">
+    <div class="col-12">
+        <div class="card">
+            <div class="card-header">
+                <h5 class="mb-0"><i class="bi bi-compass"></i> Quick Navigation</h5>
+            </div>
+            <div class="card-body">
+                <div class="row g-2">
+                    <div class="col-md-3 col-6">
+                        <a href="#getting-started" class="btn btn-outline-primary w-100">Getting Started</a>
+                    </div>
+                    <div class="col-md-3 col-6">
+                        <a href="#sites" class="btn btn-outline-primary w-100">Sites</a>
+                    </div>
+                    <div class="col-md-3 col-6">
+                        <a href="#scan-configs" class="btn btn-outline-primary w-100">Scan Configs</a>
+                    </div>
+                    <div class="col-md-3 col-6">
+                        <a href="#running-scans" class="btn btn-outline-primary w-100">Running Scans</a>
+                    </div>
+                    <div class="col-md-3 col-6">
+                        <a href="#scheduling" class="btn btn-outline-primary w-100">Scheduling</a>
+                    </div>
+                    <div class="col-md-3 col-6">
+                        <a href="#comparisons" class="btn btn-outline-primary w-100">Comparisons</a>
+                    </div>
+                    <div class="col-md-3 col-6">
+                        <a href="#alerts" class="btn btn-outline-primary w-100">Alerts</a>
+                    </div>
+                    <div class="col-md-3 col-6">
+                        <a href="#webhooks" class="btn btn-outline-primary w-100">Webhooks</a>
+                    </div>
+                </div>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Getting Started -->
+<div class="row mb-4" id="getting-started">
+    <div class="col-12">
+        <div class="card">
+            <div class="card-header">
+                <h5 class="mb-0"><i class="bi bi-rocket-takeoff"></i> Getting Started</h5>
+            </div>
+            <div class="card-body">
+                <p>SneakyScanner helps you perform network vulnerability scans and track changes over time. Here's the typical workflow:</p>
+
+                <div class="alert alert-info">
+                    <strong>Basic Workflow:</strong>
+                    <ol class="mb-0 mt-2">
+                        <li><strong>Create a Site</strong> - Define a logical grouping for your targets</li>
+                        <li><strong>Add IPs</strong> - Add IP addresses or ranges to your site</li>
+                        <li><strong>Create a Scan Config</strong> - Configure how scans should run using your site</li>
+                        <li><strong>Run a Scan</strong> - Execute scans manually or on a schedule</li>
+                        <li><strong>Review Results</strong> - Analyze findings and compare scans over time</li>
+                    </ol>
+                </div>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Sites -->
+<div class="row mb-4" id="sites">
+    <div class="col-12">
+        <div class="card">
+            <div class="card-header">
+                <h5 class="mb-0"><i class="bi bi-globe"></i> Creating Sites & Adding IPs</h5>
+            </div>
+            <div class="card-body">
+                <h6>What is a Site?</h6>
+                <p>A Site is a logical grouping of IP addresses that you want to scan together. For example, you might create separate sites for "Production Servers", "Development Environment", or "Office Network".</p>
+
+                <h6>Creating a Site</h6>
+                <ol>
+                    <li>Navigate to <strong>Configs → Sites</strong> in the navigation menu</li>
+                    <li>Click the <strong>Create Site</strong> button</li>
+                    <li>Enter a descriptive name for your site</li>
+                    <li>Optionally add a description to help identify the site's purpose</li>
+                    <li>Click <strong>Create</strong> to save the site</li>
+                </ol>
+
+                <h6>Adding IP Addresses</h6>
+                <p>After creating a site, you need to add the IP addresses you want to scan:</p>
+                <ol>
+                    <li>Find your site in the Sites list</li>
+                    <li>Click the <strong>Manage IPs</strong> button (or the site name)</li>
+                    <li>Click <strong>Add IP</strong></li>
+                    <li>Enter the IP address or CIDR range (e.g., <code>192.168.1.1</code> or <code>192.168.1.0/24</code>)</li>
+                    <li>Click <strong>Add</strong> to save</li>
+                </ol>
+
+                <div class="alert alert-warning">
+                    <i class="bi bi-exclamation-triangle"></i> <strong>Note:</strong> You can add individual IPs or CIDR notation ranges. Large ranges will result in longer scan times.
+                </div>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Scan Configs -->
+<div class="row mb-4" id="scan-configs">
+    <div class="col-12">
+        <div class="card">
+            <div class="card-header">
+                <h5 class="mb-0"><i class="bi bi-gear"></i> Creating Scan Configurations</h5>
+            </div>
+            <div class="card-body">
+                <h6>What is a Scan Config?</h6>
+                <p>A Scan Configuration defines how a scan should be performed. It links to a Site and specifies scanning parameters like ports to scan, timing options, and other settings.</p>
+
+                <h6>Creating a Scan Config</h6>
+                <ol>
+                    <li>Navigate to <strong>Configs → Scan Configs</strong> in the navigation menu</li>
+                    <li>Click the <strong>Create Config</strong> button</li>
+                    <li>Enter a name for the configuration</li>
+                    <li>Select the <strong>Site</strong> to associate with this config</li>
+                    <li>Configure scan parameters:
+                        <ul>
+                            <li><strong>Ports</strong> - Specify ports to scan (e.g., <code>22,80,443</code> or <code>1-1000</code>)</li>
+                            <li><strong>Timing</strong> - Set scan speed/aggressiveness</li>
+                            <li><strong>Additional Options</strong> - Configure other nmap parameters as needed</li>
+                        </ul>
+                    </li>
+                    <li>Click <strong>Create</strong> to save the configuration</li>
+                </ol>
+
+                <div class="alert alert-info">
+                    <i class="bi bi-info-circle"></i> <strong>Tip:</strong> Create different configs for different purposes - a quick config for daily checks and a thorough config for weekly deep scans.
+                </div>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Running Scans -->
+<div class="row mb-4" id="running-scans">
+    <div class="col-12">
+        <div class="card">
+            <div class="card-header">
+                <h5 class="mb-0"><i class="bi bi-play-circle"></i> Running Scans</h5>
+            </div>
+            <div class="card-body">
+                <h6>Starting a Manual Scan</h6>
+                <ol>
+                    <li>Navigate to <strong>Scans</strong> in the navigation menu</li>
+                    <li>Click the <strong>New Scan</strong> button</li>
+                    <li>Select the <strong>Scan Config</strong> you want to use</li>
+                    <li>Click <strong>Start Scan</strong></li>
+                </ol>
+
+                <h6>Monitoring Scan Progress</h6>
+                <p>While a scan is running:</p>
+                <ul>
+                    <li>The scan will appear in the Scans list with a <span class="badge badge-warning">Running</span> status</li>
+                    <li>You can view live progress by clicking on the scan</li>
+                    <li>The Dashboard also shows active scans</li>
+                </ul>
+
+                <h6>Viewing Scan Results</h6>
+                <ol>
+                    <li>Once complete, click on a scan in the Scans list</li>
+                    <li>View discovered hosts, open ports, and services</li>
+                    <li>Export results or compare with previous scans</li>
+                </ol>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Scheduling -->
+<div class="row mb-4" id="scheduling">
+    <div class="col-12">
+        <div class="card">
+            <div class="card-header">
+                <h5 class="mb-0"><i class="bi bi-calendar-check"></i> Scheduling Scans</h5>
+            </div>
+            <div class="card-body">
+                <h6>Why Schedule Scans?</h6>
+                <p>Scheduled scans allow you to automatically run scans at regular intervals, ensuring continuous monitoring of your network without manual intervention.</p>
+
+                <h6>Creating a Schedule</h6>
+                <ol>
+                    <li>Navigate to <strong>Schedules</strong> in the navigation menu</li>
+                    <li>Click the <strong>Create Schedule</strong> button</li>
+                    <li>Enter a name for the schedule</li>
+                    <li>Select the <strong>Scan Config</strong> to use</li>
+                    <li>Configure the schedule:
+                        <ul>
+                            <li><strong>Frequency</strong> - How often to run (daily, weekly, monthly, custom cron)</li>
+                            <li><strong>Time</strong> - When to start the scan</li>
+                            <li><strong>Days</strong> - Which days to run (for weekly schedules)</li>
+                        </ul>
+                    </li>
+                    <li>Enable/disable the schedule as needed</li>
+                    <li>Click <strong>Create</strong> to save</li>
+                </ol>
+
+                <h6>Managing Schedules</h6>
+                <ul>
+                    <li><strong>Enable/Disable</strong> - Toggle schedules on or off without deleting them</li>
+                    <li><strong>Edit</strong> - Modify the schedule timing or associated config</li>
+                    <li><strong>Delete</strong> - Remove schedules you no longer need</li>
+                    <li><strong>View History</strong> - See past runs triggered by the schedule</li>
+                </ul>
+
+                <div class="alert alert-info">
+                    <i class="bi bi-info-circle"></i> <strong>Tip:</strong> Schedule comprehensive scans during off-peak hours to minimize network impact.
+                </div>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Scan Comparisons -->
+<div class="row mb-4" id="comparisons">
+    <div class="col-12">
+        <div class="card">
+            <div class="card-header">
+                <h5 class="mb-0"><i class="bi bi-arrow-left-right"></i> Scan Comparisons</h5>
+            </div>
+            <div class="card-body">
+                <h6>Why Compare Scans?</h6>
+                <p>Comparing scans helps you identify changes in your network over time - new hosts, closed ports, new services, or potential security issues.</p>
+
+                <h6>Comparing Two Scans</h6>
+                <ol>
+                    <li>Navigate to <strong>Scans</strong> in the navigation menu</li>
+                    <li>Find the scan you want to use as the baseline</li>
+                    <li>Click on the scan to view its details</li>
+                    <li>Click the <strong>Compare</strong> button</li>
+                    <li>Select another scan to compare against</li>
+                    <li>Review the comparison results</li>
+                </ol>
+
+                <h6>Understanding Comparison Results</h6>
+                <p>The comparison view shows:</p>
+                <ul>
+                    <li><span class="badge badge-success">New</span> - Hosts or ports that appear in the newer scan but not the older one</li>
+                    <li><span class="badge badge-danger">Removed</span> - Hosts or ports that were in the older scan but not the newer one</li>
+                    <li><span class="badge badge-warning">Changed</span> - Services or states that differ between scans</li>
+                    <li><span class="badge badge-info">Unchanged</span> - Items that remain the same</li>
+                </ul>
+
+                <div class="alert alert-warning">
+                    <i class="bi bi-exclamation-triangle"></i> <strong>Security Note:</strong> Pay close attention to unexpected new open ports or services - these could indicate unauthorized changes or potential compromises.
+                </div>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Alerts -->
+<div class="row mb-4" id="alerts">
+    <div class="col-12">
+        <div class="card">
+            <div class="card-header">
+                <h5 class="mb-0"><i class="bi bi-bell"></i> Alerts & Alert Rules</h5>
+            </div>
+            <div class="card-body">
+                <h6>Understanding Alerts</h6>
+                <p>Alerts notify you when scan results match certain conditions you define. This helps you stay informed about important changes without manually reviewing every scan.</p>
+
+                <h6>Viewing Alert History</h6>
+                <ol>
+                    <li>Navigate to <strong>Alerts → Alert History</strong></li>
+                    <li>View all triggered alerts with timestamps and details</li>
+                    <li>Filter alerts by severity, date, or type</li>
+                    <li>Click on an alert to see full details and the associated scan</li>
+                </ol>
+
+                <h6>Creating Alert Rules</h6>
+                <ol>
+                    <li>Navigate to <strong>Alerts → Alert Rules</strong></li>
+                    <li>Click <strong>Create Rule</strong></li>
+                    <li>Configure the rule:
+                        <ul>
+                            <li><strong>Name</strong> - A descriptive name for the rule</li>
+                            <li><strong>Condition</strong> - What triggers the alert (e.g., new open port, new host, specific service detected)</li>
+                            <li><strong>Severity</strong> - How critical is this alert (Info, Warning, Critical)</li>
+                            <li><strong>Scope</strong> - Which sites or configs this rule applies to</li>
+                        </ul>
+                    </li>
+                    <li>Enable the rule</li>
+                    <li>Click <strong>Create</strong> to save</li>
+                </ol>
+
+                <h6>Common Alert Rule Examples</h6>
+                <ul>
+                    <li><strong>New Host Detected</strong> - Alert when a previously unknown host appears</li>
+                    <li><strong>New Open Port</strong> - Alert when a new port opens on any host</li>
+                    <li><strong>Critical Port Open</strong> - Alert for specific high-risk ports (e.g., 23/Telnet, 3389/RDP)</li>
+                    <li><strong>Service Change</strong> - Alert when a service version changes</li>
+                    <li><strong>Host Offline</strong> - Alert when an expected host stops responding</li>
+                </ul>
+
+                <div class="alert alert-info">
+                    <i class="bi bi-info-circle"></i> <strong>Tip:</strong> Start with a few important rules and refine them over time to avoid alert fatigue.
+                </div>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Webhooks -->
+<div class="row mb-4" id="webhooks">
+    <div class="col-12">
+        <div class="card">
+            <div class="card-header">
+                <h5 class="mb-0"><i class="bi bi-broadcast"></i> Webhooks</h5>
+            </div>
+            <div class="card-body">
+                <h6>What are Webhooks?</h6>
+                <p>Webhooks allow SneakyScanner to send notifications to external services when events occur, such as scan completion or alert triggers. This enables integration with tools like Slack, Discord, Microsoft Teams, or custom systems.</p>
+
+                <h6>Creating a Webhook</h6>
+                <ol>
+                    <li>Navigate to <strong>Alerts → Webhooks</strong></li>
+                    <li>Click <strong>Create Webhook</strong></li>
+                    <li>Configure the webhook:
+                        <ul>
+                            <li><strong>Name</strong> - A descriptive name</li>
+                            <li><strong>URL</strong> - The endpoint to send notifications to</li>
+                            <li><strong>Events</strong> - Which events trigger this webhook</li>
+                            <li><strong>Secret</strong> - Optional secret for request signing</li>
+                        </ul>
+                    </li>
+                    <li>Test the webhook to verify it works</li>
+                    <li>Click <strong>Create</strong> to save</li>
+                </ol>
+
+                <h6>Webhook Events</h6>
+                <ul>
+                    <li><strong>Scan Started</strong> - When a scan begins</li>
+                    <li><strong>Scan Completed</strong> - When a scan finishes</li>
+                    <li><strong>Scan Failed</strong> - When a scan encounters an error</li>
+                    <li><strong>Alert Triggered</strong> - When an alert rule matches</li>
+                </ul>
+
+                <h6>Integration Examples</h6>
+                <ul>
+                    <li><strong>Slack</strong> - Use a Slack Incoming Webhook URL</li>
+                    <li><strong>Discord</strong> - Use a Discord Webhook URL</li>
+                    <li><strong>Microsoft Teams</strong> - Use a Teams Incoming Webhook</li>
+                    <li><strong>Custom API</strong> - Send to your own endpoint for custom processing</li>
+                </ul>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Back to Top -->
+<div class="row mb-4">
+    <div class="col-12 text-center">
+        <a href="#" class="btn btn-outline-secondary">
+            <i class="bi bi-arrow-up"></i> Back to Top
+        </a>
+    </div>
+</div>
+
+{% endblock %}

app/web/templates/ip_search_results.html

@@ -0,0 +1,175 @@
+{% extends "base.html" %}
+
+{% block title %}Search Results for {{ ip_address }} - SneakyScanner{% endblock %}
+
+{% block content %}
+<div class="row mt-4">
+    <div class="col-12 d-flex justify-content-between align-items-center mb-4">
+        <h1>
+            <i class="bi bi-search"></i>
+            Search Results
+            {% if ip_address %}
+            <small class="text-muted">for {{ ip_address }}</small>
+            {% endif %}
+        </h1>
+        <a href="{{ url_for('main.scans') }}" class="btn btn-secondary">
+            <i class="bi bi-arrow-left"></i> Back to Scans
+        </a>
+    </div>
+</div>
+
+{% if not ip_address %}
+<!-- No IP provided -->
+<div class="row">
+    <div class="col-12">
+        <div class="card">
+            <div class="card-body text-center py-5">
+                <i class="bi bi-exclamation-circle text-warning" style="font-size: 3rem;"></i>
+                <h4 class="mt-3">No IP Address Provided</h4>
+                <p class="text-muted">Please enter an IP address in the search box to find related scans.</p>
+            </div>
+        </div>
+    </div>
+</div>
+{% else %}
+<!-- Results Table -->
+<div class="row">
+    <div class="col-12">
+        <div class="card">
+            <div class="card-header">
+                <h5 class="mb-0">Last 10 Scans Containing {{ ip_address }}</h5>
+            </div>
+            <div class="card-body">
+                <div id="results-loading" class="text-center py-5">
+                    <div class="spinner-border" role="status">
+                        <span class="visually-hidden">Loading...</span>
+                    </div>
+                    <p class="mt-3 text-muted">Searching for scans...</p>
+                </div>
+                <div id="results-error" class="alert alert-danger" style="display: none;"></div>
+                <div id="results-empty" class="text-center py-5 text-muted" style="display: none;">
+                    <i class="bi bi-search" style="font-size: 3rem;"></i>
+                    <h5 class="mt-3">No Scans Found</h5>
+                    <p>No completed scans contain the IP address <strong>{{ ip_address }}</strong>.</p>
+                </div>
+                <div id="results-table-container" style="display: none;">
+                    <div class="table-responsive">
+                        <table class="table table-hover">
+                            <thead>
+                                <tr>
+                                    <th style="width: 80px;">ID</th>
+                                    <th>Title</th>
+                                    <th style="width: 200px;">Timestamp</th>
+                                    <th style="width: 100px;">Duration</th>
+                                    <th style="width: 120px;">Status</th>
+                                    <th style="width: 100px;">Actions</th>
+                                </tr>
+                            </thead>
+                            <tbody id="results-tbody">
+                            </tbody>
+                        </table>
+                    </div>
+                    <div class="text-muted mt-3">
+                        Found <span id="result-count">0</span> scan(s) containing this IP address.
+                    </div>
+                </div>
+            </div>
+        </div>
+    </div>
+</div>
+{% endif %}
+{% endblock %}
+
+{% block scripts %}
+<script>
+    const ipAddress = "{{ ip_address | e }}";
+
+    // Load results when page loads
+    document.addEventListener('DOMContentLoaded', function() {
+        if (ipAddress) {
+            loadResults();
+        }
+    });
+
+    // Load search results from API
+    async function loadResults() {
+        const loadingEl = document.getElementById('results-loading');
+        const errorEl = document.getElementById('results-error');
+        const emptyEl = document.getElementById('results-empty');
+        const tableEl = document.getElementById('results-table-container');
+
+        // Show loading state
+        loadingEl.style.display = 'block';
+        errorEl.style.display = 'none';
+        emptyEl.style.display = 'none';
+        tableEl.style.display = 'none';
+
+        try {
+            const response = await fetch(`/api/scans/by-ip/${encodeURIComponent(ipAddress)}`);
+            if (!response.ok) {
+                throw new Error('Failed to search for scans');
+            }
+
+            const data = await response.json();
+            const scans = data.scans || [];
+
+            loadingEl.style.display = 'none';
+
+            if (scans.length === 0) {
+                emptyEl.style.display = 'block';
+            } else {
+                tableEl.style.display = 'block';
+                renderResultsTable(scans);
+                document.getElementById('result-count').textContent = data.count;
+            }
+        } catch (error) {
+            console.error('Error searching for scans:', error);
+            loadingEl.style.display = 'none';
+            errorEl.textContent = 'Failed to search for scans. Please try again.';
+            errorEl.style.display = 'block';
+        }
+    }
+
+    // Render results table
+    function renderResultsTable(scans) {
+        const tbody = document.getElementById('results-tbody');
+        tbody.innerHTML = '';
+
+        scans.forEach(scan => {
+            const row = document.createElement('tr');
+            row.classList.add('scan-row');
+
+            // Format timestamp
+            const timestamp = new Date(scan.timestamp).toLocaleString();
+
+            // Format duration
+            const duration = scan.duration ? `${scan.duration.toFixed(1)}s` : '-';
+
+            // Status badge
+            let statusBadge = '';
+            if (scan.status === 'completed') {
+                statusBadge = '<span class="badge badge-success">Completed</span>';
+            } else if (scan.status === 'running') {
+                statusBadge = '<span class="badge badge-info">Running</span>';
+            } else if (scan.status === 'failed') {
+                statusBadge = '<span class="badge badge-danger">Failed</span>';
+            } else {
+                statusBadge = `<span class="badge badge-info">${scan.status}</span>`;
+            }
+
+            row.innerHTML = `
+                <td class="mono">${scan.id}</td>
+                <td>${scan.title || 'Untitled Scan'}</td>
+                <td class="text-muted">${timestamp}</td>
+                <td class="mono">${duration}</td>
+                <td>${statusBadge}</td>
+                <td>
+                    <a href="/scans/${scan.id}" class="btn btn-sm btn-secondary">View</a>
+                </td>
+            `;
+
+            tbody.appendChild(row);
+        });
+    }
+</script>
+{% endblock %}

app/web/templates/login.html

@@ -2,57 +2,6 @@
 
 {% block title %}Login - SneakyScanner{% endblock %}
 
-{% block extra_styles %}
-body {
-    height: 100vh;
-    display: flex;
-    align-items: center;
-    justify-content: center;
-    background: linear-gradient(135deg, #0f172a 0%, #1e293b 100%);
-}
-
-.container-fluid {
-    max-width: 450px;
-    padding: 0;
-}
-
-.login-card {
-    background-color: #1e293b;
-    border: 1px solid #334155;
-    border-radius: 12px;
-    padding: 3rem;
-    box-shadow: 0 8px 32px rgba(0, 0, 0, 0.3);
-}
-
-.brand-title {
-    color: #60a5fa;
-    font-weight: 600;
-    font-size: 2rem;
-    margin-bottom: 0.5rem;
-}
-
-.brand-subtitle {
-    color: #94a3b8;
-    font-size: 0.95rem;
-}
-
-.btn-primary {
-    padding: 0.75rem;
-    font-size: 1rem;
-    font-weight: 500;
-}
-
-.footer {
-    position: fixed;
-    bottom: 20px;
-    left: 0;
-    right: 0;
-    margin: 0;
-    padding: 0;
-    border: none;
-}
-{% endblock %}
-
 {% set hide_nav = true %}
 
 {% block content %}

app/web/templates/scan_compare.html

@@ -28,6 +28,13 @@
 <!-- Error State -->
 <div id="comparison-error" class="alert alert-danger" style="display: none;"></div>
 
+<!-- Config Warning -->
+<div id="config-warning" class="alert alert-warning" style="display: none;">
+    <i class="bi bi-exclamation-triangle"></i>
+    <strong>Different Configurations Detected</strong>
+    <p class="mb-0" id="config-warning-message"></p>
+</div>
+
 <!-- Comparison Content -->
 <div id="comparison-content" style="display: none;">
     <!-- Drift Score Card -->
@@ -52,14 +59,16 @@
                                     <div class="mb-3">
                                         <label class="form-label text-muted">Older Scan (#<span id="scan1-id"></span>)</label>
                                         <div id="scan1-title" class="fw-bold">-</div>
-                                        <small class="text-muted" id="scan1-timestamp">-</small>
+                                        <small class="text-muted d-block" id="scan1-timestamp">-</small>
+                                        <small class="text-muted d-block"><i class="bi bi-file-earmark-text"></i> <span id="scan1-config">-</span></small>
                                     </div>
                                 </div>
                                 <div class="col-md-4">
                                     <div class="mb-3">
                                         <label class="form-label text-muted">Newer Scan (#<span id="scan2-id"></span>)</label>
                                         <div id="scan2-title" class="fw-bold">-</div>
-                                        <small class="text-muted" id="scan2-timestamp">-</small>
+                                        <small class="text-muted d-block" id="scan2-timestamp">-</small>
+                                        <small class="text-muted d-block"><i class="bi bi-file-earmark-text"></i> <span id="scan2-config">-</span></small>
                                     </div>
                                 </div>
                                 <div class="col-md-4">
@@ -340,6 +349,14 @@
     }
 
     function populateComparison(data) {
+        // Show config warning if configs differ
+        if (data.config_warning) {
+            const warningDiv = document.getElementById('config-warning');
+            const warningMessage = document.getElementById('config-warning-message');
+            warningMessage.textContent = data.config_warning;
+            warningDiv.style.display = 'block';
+        }
+
         // Drift score
         const driftScore = data.drift_score || 0;
         document.getElementById('drift-score').textContent = driftScore.toFixed(3);
@@ -358,10 +375,12 @@
         document.getElementById('scan1-id').textContent = data.scan1.id;
         document.getElementById('scan1-title').textContent = data.scan1.title || 'Untitled Scan';
         document.getElementById('scan1-timestamp').textContent = new Date(data.scan1.timestamp).toLocaleString();
+        document.getElementById('scan1-config').textContent = data.scan1.config_id || 'Unknown';
 
         document.getElementById('scan2-id').textContent = data.scan2.id;
         document.getElementById('scan2-title').textContent = data.scan2.title || 'Untitled Scan';
         document.getElementById('scan2-timestamp').textContent = new Date(data.scan2.timestamp).toLocaleString();
+        document.getElementById('scan2-config').textContent = data.scan2.config_id || 'Unknown';
 
         // Ports comparison
         populatePortsComparison(data.ports);

app/web/templates/scans.html

@@ -5,7 +5,7 @@
 {% block content %}
 <div class="row mt-4">
     <div class="col-12 d-flex justify-content-between align-items-center mb-4">
-        <h1 style="color: #60a5fa;">All Scans</h1>
+        <h1>All Scans</h1>
         <button class="btn btn-primary" onclick="showTriggerScanModal()">
             <span id="trigger-btn-text">Trigger New Scan</span>
             <span id="trigger-btn-spinner" class="spinner-border spinner-border-sm ms-2" style="display: none;"></span>
@@ -26,6 +26,7 @@
                             <option value="running">Running</option>
                             <option value="completed">Completed</option>
                             <option value="failed">Failed</option>
+                            <option value="cancelled">Cancelled</option>
                         </select>
                     </div>
                     <div class="col-md-4">
@@ -54,7 +55,7 @@
     <div class="col-12">
         <div class="card">
             <div class="card-header">
-                <h5 class="mb-0" style="color: #60a5fa;">Scan History</h5>
+                <h5 class="mb-0">Scan History</h5>
             </div>
             <div class="card-body">
                 <div id="scans-loading" class="text-center py-5">
@@ -105,35 +106,36 @@
 <!-- Trigger Scan Modal -->
 <div class="modal fade" id="triggerScanModal" tabindex="-1">
     <div class="modal-dialog">
-        <div class="modal-content" style="background-color: #1e293b; border: 1px solid #334155;">
-            <div class="modal-header" style="border-bottom: 1px solid #334155;">
-                <h5 class="modal-title" style="color: #60a5fa;">Trigger New Scan</h5>
+        <div class="modal-content">
+            <div class="modal-header">
+                <h5 class="modal-title">Trigger New Scan</h5>
                 <button type="button" class="btn-close" data-bs-dismiss="modal"></button>
             </div>
             <div class="modal-body">
                 <form id="trigger-scan-form">
                     <div class="mb-3">
-                        <label for="config-file" class="form-label">Config File</label>
-                        <select class="form-select" id="config-file" name="config_file" required>
-                            <option value="">Select a config file...</option>
-                            {% for config in config_files %}
-                            <option value="{{ config }}">{{ config }}</option>
-                            {% endfor %}
+                        <label for="config-select" class="form-label">Scan Configuration</label>
+                        <select class="form-select" id="config-select" name="config_id" required>
+                            <option value="">Loading configurations...</option>
                         </select>
-                        <div class="form-text text-muted">
-                            {% if config_files %}
-                                Select a scan configuration file
-                            {% else %}
-                                <span class="text-warning">No config files found in /app/configs/</span>
-                            {% endif %}
+                        <div class="form-text text-muted" id="config-help-text">
+                            Select a scan configuration
+                        </div>
+                        <div id="no-configs-warning" class="alert alert-warning mt-2 mb-0" role="alert" style="display: none;">
+                            <i class="bi bi-exclamation-triangle"></i>
+                            <strong>No configurations available</strong>
+                            <p class="mb-2 mt-2">You need to create a configuration before you can trigger a scan.</p>
+                            <a href="{{ url_for('main.configs') }}" class="btn btn-sm btn-primary">
+                                <i class="bi bi-plus-circle"></i> Create Configuration
+                            </a>
                         </div>
                     </div>
                     <div id="trigger-error" class="alert alert-danger" style="display: none;"></div>
                 </form>
             </div>
-            <div class="modal-footer" style="border-top: 1px solid #334155;">
+            <div class="modal-footer">
                 <button type="button" class="btn btn-secondary" data-bs-dismiss="modal">Cancel</button>
-                <button type="button" class="btn btn-primary" onclick="triggerScan()">
+                <button type="button" class="btn btn-primary" id="trigger-scan-btn" onclick="triggerScan()">
                     <span id="modal-trigger-text">Trigger Scan</span>
                     <span id="modal-trigger-spinner" class="spinner-border spinner-border-sm ms-2" style="display: none;"></span>
                 </button>
@@ -150,6 +152,25 @@
     let statusFilter = '';
     let totalCount = 0;
 
+    // Show alert notification
+    function showAlert(type, message) {
+        const container = document.getElementById('notification-container');
+        const notification = document.createElement('div');
+        notification.className = `alert alert-${type} alert-dismissible fade show mb-2`;
+
+        notification.innerHTML = `
+            ${message}
+            <button type="button" class="btn-close" data-bs-dismiss="alert"></button>
+        `;
+
+        container.appendChild(notification);
+
+        // Auto-dismiss after 5 seconds
+        setTimeout(() => {
+            notification.remove();
+        }, 5000);
+    }
+
     // Load initial data when page loads
     document.addEventListener('DOMContentLoaded', function() {
         loadScans();
@@ -228,20 +249,27 @@
                 statusBadge = '<span class="badge badge-info">Running</span>';
             } else if (scan.status === 'failed') {
                 statusBadge = '<span class="badge badge-danger">Failed</span>';
+            } else if (scan.status === 'cancelled') {
+                statusBadge = '<span class="badge badge-warning">Cancelled</span>';
             } else {
                 statusBadge = `<span class="badge badge-info">${scan.status}</span>`;
             }
 
+            // Action buttons
+            let actionButtons = `<a href="/scans/${scan.id}" class="btn btn-sm btn-secondary">View</a>`;
+            if (scan.status === 'running') {
+                actionButtons += `<button class="btn btn-sm btn-warning ms-1" onclick="stopScan(${scan.id})">Stop</button>`;
+            } else {
+                actionButtons += `<button class="btn btn-sm btn-danger ms-1" onclick="deleteScan(${scan.id})">Delete</button>`;
+            }
+
             row.innerHTML = `
                 <td class="mono">${scan.id}</td>
                 <td>${scan.title || 'Untitled Scan'}</td>
                 <td class="text-muted">${timestamp}</td>
                 <td class="mono">${duration}</td>
                 <td>${statusBadge}</td>
-                <td>
-                    <a href="/scans/${scan.id}" class="btn btn-sm btn-secondary">View</a>
-                    ${scan.status !== 'running' ? `<button class="btn btn-sm btn-danger ms-1" onclick="deleteScan(${scan.id})">Delete</button>` : ''}
-                </td>
+                <td>${actionButtons}</td>
             `;
 
             tbody.appendChild(row);
@@ -352,23 +380,75 @@
         });
     }
 
+    // Load available configs
+    async function loadConfigs() {
+        const selectEl = document.getElementById('config-select');
+        const helpTextEl = document.getElementById('config-help-text');
+        const noConfigsWarning = document.getElementById('no-configs-warning');
+        const triggerBtn = document.getElementById('trigger-scan-btn');
+
+        try {
+            const response = await fetch('/api/configs');
+            if (!response.ok) {
+                throw new Error('Failed to load configurations');
+            }
+
+            const data = await response.json();
+            const configs = data.configs || [];
+
+            // Clear existing options
+            selectEl.innerHTML = '';
+
+            if (configs.length === 0) {
+                selectEl.innerHTML = '<option value="">No configurations available</option>';
+                selectEl.disabled = true;
+                triggerBtn.disabled = true;
+                helpTextEl.style.display = 'none';
+                noConfigsWarning.style.display = 'block';
+            } else {
+                selectEl.innerHTML = '<option value="">Select a configuration...</option>';
+                configs.forEach(config => {
+                    const option = document.createElement('option');
+                    option.value = config.id;
+                    const siteText = config.site_count === 1 ? 'site' : 'sites';
+                    option.textContent = `${config.title} (${config.site_count} ${siteText})`;
+                    selectEl.appendChild(option);
+                });
+                selectEl.disabled = false;
+                triggerBtn.disabled = false;
+                helpTextEl.style.display = 'block';
+                noConfigsWarning.style.display = 'none';
+            }
+        } catch (error) {
+            console.error('Error loading configs:', error);
+            selectEl.innerHTML = '<option value="">Error loading configurations</option>';
+            selectEl.disabled = true;
+            triggerBtn.disabled = true;
+            helpTextEl.style.display = 'none';
+        }
+    }
+
     // Show trigger scan modal
     function showTriggerScanModal() {
         const modal = new bootstrap.Modal(document.getElementById('triggerScanModal'));
         document.getElementById('trigger-error').style.display = 'none';
         document.getElementById('trigger-scan-form').reset();
+
+        // Load configs when modal is shown
+        loadConfigs();
+
         modal.show();
     }
 
     // Trigger scan
     async function triggerScan() {
-        const configFile = document.getElementById('config-file').value;
+        const configId = document.getElementById('config-select').value;
         const errorEl = document.getElementById('trigger-error');
         const btnText = document.getElementById('modal-trigger-text');
         const btnSpinner = document.getElementById('modal-trigger-spinner');
 
-        if (!configFile) {
-            errorEl.textContent = 'Please enter a config file path.';
+        if (!configId) {
+            errorEl.textContent = 'Please select a configuration.';
             errorEl.style.display = 'block';
             return;
         }
@@ -385,28 +465,25 @@
                     'Content-Type': 'application/json',
                 },
                 body: JSON.stringify({
-                    config_file: configFile
+                    config_id: parseInt(configId)
                 })
             });
 
             if (!response.ok) {
                 const data = await response.json();
-                throw new Error(data.error || 'Failed to trigger scan');
+                throw new Error(data.message || data.error || 'Failed to trigger scan');
             }
 
             const data = await response.json();
 
+            // Hide error before closing modal to prevent flash
+            errorEl.style.display = 'none';
+
             // Close modal
             bootstrap.Modal.getInstance(document.getElementById('triggerScanModal')).hide();
 
             // Show success message
-            const alertDiv = document.createElement('div');
-            alertDiv.className = 'alert alert-success alert-dismissible fade show mt-3';
-            alertDiv.innerHTML = `
-                Scan triggered successfully! (ID: ${data.scan_id})
-                <button type="button" class="btn-close" data-bs-dismiss="alert"></button>
-            `;
-            document.querySelector('.container-fluid').insertBefore(alertDiv, document.querySelector('.row'));
+            showAlert('success', `Scan triggered successfully! (ID: ${data.scan_id})`);
 
             // Refresh scans
             loadScans();
@@ -420,6 +497,33 @@
         }
     }
 
+    // Stop scan
+    async function stopScan(scanId) {
+        if (!confirm(`Are you sure you want to stop scan ${scanId}?`)) {
+            return;
+        }
+
+        try {
+            const response = await fetch(`/api/scans/${scanId}/stop`, {
+                method: 'POST'
+            });
+
+            if (!response.ok) {
+                const data = await response.json();
+                throw new Error(data.message || 'Failed to stop scan');
+            }
+
+            // Show success message
+            showAlert('success', `Stop signal sent to scan ${scanId}.`);
+
+            // Refresh scans after a short delay
+            setTimeout(() => loadScans(), 1000);
+        } catch (error) {
+            console.error('Error stopping scan:', error);
+            showAlert('danger', `Failed to stop scan: ${error.message}`);
+        }
+    }
+
     // Delete scan
     async function deleteScan(scanId) {
         if (!confirm(`Are you sure you want to delete scan ${scanId}?`)) {
@@ -432,44 +536,20 @@
             });
 
             if (!response.ok) {
-                throw new Error('Failed to delete scan');
+                const data = await response.json();
+                throw new Error(data.message || 'Failed to delete scan');
             }
 
             // Show success message
-            const alertDiv = document.createElement('div');
-            alertDiv.className = 'alert alert-success alert-dismissible fade show mt-3';
-            alertDiv.innerHTML = `
-                Scan ${scanId} deleted successfully.
-                <button type="button" class="btn-close" data-bs-dismiss="alert"></button>
-            `;
-            document.querySelector('.container-fluid').insertBefore(alertDiv, document.querySelector('.row'));
+            showAlert('success', `Scan ${scanId} deleted successfully.`);
 
             // Refresh scans
             loadScans();
         } catch (error) {
             console.error('Error deleting scan:', error);
-            alert('Failed to delete scan. Please try again.');
+            showAlert('danger', `Failed to delete scan: ${error.message}`);
         }
     }
 
-    // Custom pagination styles
-    const style = document.createElement('style');
-    style.textContent = `
-        .pagination {
-            --bs-pagination-bg: #1e293b;
-            --bs-pagination-border-color: #334155;
-            --bs-pagination-hover-bg: #334155;
-            --bs-pagination-hover-border-color: #475569;
-            --bs-pagination-focus-bg: #334155;
-            --bs-pagination-active-bg: #3b82f6;
-            --bs-pagination-active-border-color: #3b82f6;
-            --bs-pagination-disabled-bg: #0f172a;
-            --bs-pagination-disabled-border-color: #334155;
-            --bs-pagination-color: #e2e8f0;
-            --bs-pagination-hover-color: #e2e8f0;
-            --bs-pagination-disabled-color: #64748b;
-        }
-    `;
-    document.head.appendChild(style);
 </script>
 {% endblock %}

app/web/templates/schedule_create.html

@@ -32,13 +32,13 @@
                         <small class="form-text text-muted">A descriptive name for this schedule</small>
                     </div>
 
-                    <!-- Config File -->
+                    <!-- Config -->
                     <div class="mb-3">
-                        <label for="config-file" class="form-label">Configuration File <span class="text-danger">*</span></label>
-                        <select class="form-select" id="config-file" name="config_file" required>
-                            <option value="">Select a configuration file...</option>
-                            {% for config in config_files %}
-                            <option value="{{ config }}">{{ config }}</option>
+                        <label for="config-id" class="form-label">Configuration <span class="text-danger">*</span></label>
+                        <select class="form-select" id="config-id" name="config_id" required>
+                            <option value="">Select a configuration...</option>
+                            {% for config in configs %}
+                            <option value="{{ config.id }}">{{ config.title }}</option>
                             {% endfor %}
                         </select>
                         <small class="form-text text-muted">The scan configuration to use for this schedule</small>
@@ -369,13 +369,13 @@ document.getElementById('create-schedule-form').addEventListener('submit', async
     // Get form data
     const formData = {
         name: document.getElementById('schedule-name').value.trim(),
-        config_file: document.getElementById('config-file').value,
+        config_id: parseInt(document.getElementById('config-id').value),
         cron_expression: document.getElementById('cron-expression').value.trim(),
         enabled: document.getElementById('schedule-enabled').checked
     };
 
     // Validate
-    if (!formData.name || !formData.config_file || !formData.cron_expression) {
+    if (!formData.name || !formData.config_id || !formData.cron_expression) {
         showNotification('Please fill in all required fields', 'warning');
         return;
     }
@@ -419,19 +419,16 @@ document.getElementById('create-schedule-form').addEventListener('submit', async
 
 // Show notification
 function showNotification(message, type = 'info') {
+    const container = document.getElementById('notification-container');
     const notification = document.createElement('div');
-    notification.className = `alert alert-${type} alert-dismissible fade show position-fixed`;
-    notification.style.top = '20px';
-    notification.style.right = '20px';
-    notification.style.zIndex = '9999';
-    notification.style.minWidth = '300px';
+    notification.className = `alert alert-${type} alert-dismissible fade show mb-2`;
 
     notification.innerHTML = `
         ${message}
         <button type="button" class="btn-close" data-bs-dismiss="alert"></button>
     `;
 
-    document.body.appendChild(notification);
+    container.appendChild(notification);
 
     setTimeout(() => {
         notification.remove();

app/web/templates/schedule_edit.html

@@ -298,7 +298,11 @@ async function loadSchedule() {
 function populateForm(schedule) {
     document.getElementById('schedule-id').value = schedule.id;
     document.getElementById('schedule-name').value = schedule.name;
-    document.getElementById('config-file').value = schedule.config_file;
+    // Display config name and ID in the readonly config-file field
+    const configDisplay = schedule.config_name
+        ? `${schedule.config_name} (ID: ${schedule.config_id})`
+        : `Config ID: ${schedule.config_id}`;
+    document.getElementById('config-file').value = configDisplay;
     document.getElementById('cron-expression').value = schedule.cron_expression;
     document.getElementById('schedule-enabled').checked = schedule.enabled;
 
@@ -554,19 +558,16 @@ async function deleteSchedule() {
 
 // Show notification
 function showNotification(message, type = 'info') {
+    const container = document.getElementById('notification-container');
     const notification = document.createElement('div');
-    notification.className = `alert alert-${type} alert-dismissible fade show position-fixed`;
-    notification.style.top = '20px';
-    notification.style.right = '20px';
-    notification.style.zIndex = '9999';
-    notification.style.minWidth = '300px';
+    notification.className = `alert alert-${type} alert-dismissible fade show mb-2`;
 
     notification.innerHTML = `
         ${message}
         <button type="button" class="btn-close" data-bs-dismiss="alert"></button>
     `;
 
-    document.body.appendChild(notification);
+    container.appendChild(notification);
 
     setTimeout(() => {
         notification.remove();

app/web/templates/schedules.html

@@ -6,7 +6,7 @@
 <div class="row mt-4">
     <div class="col-12">
         <div class="d-flex justify-content-between align-items-center mb-4">
-            <h1 style="color: #60a5fa;">Scheduled Scans</h1>
+            <h1>Scheduled Scans</h1>
             <a href="{{ url_for('main.create_schedule') }}" class="btn btn-primary">
                 <i class="bi bi-plus-circle"></i> New Schedule
             </a>
@@ -47,7 +47,7 @@
     <div class="col-12">
         <div class="card">
             <div class="card-header">
-                <h5 class="mb-0" style="color: #60a5fa;">All Schedules</h5>
+                <h5 class="mb-0">All Schedules</h5>
             </div>
             <div class="card-body">
                 <div id="schedules-loading" class="text-center py-5">
@@ -198,7 +198,7 @@ function renderSchedules() {
             <td>
                 <strong>${escapeHtml(schedule.name)}</strong>
                 <br>
-                <small class="text-muted">${escapeHtml(schedule.config_file)}</small>
+                <small class="text-muted">Config ID: ${schedule.config_id || 'N/A'}</small>
             </td>
             <td class="mono"><code>${escapeHtml(schedule.cron_expression)}</code></td>
             <td>${formatRelativeTime(schedule.next_run)}</td>
@@ -352,20 +352,16 @@ async function deleteSchedule(scheduleId) {
 
 // Show notification
 function showNotification(message, type = 'info') {
-    // Create notification element
+    const container = document.getElementById('notification-container');
     const notification = document.createElement('div');
-    notification.className = `alert alert-${type} alert-dismissible fade show position-fixed`;
-    notification.style.top = '20px';
-    notification.style.right = '20px';
-    notification.style.zIndex = '9999';
-    notification.style.minWidth = '300px';
+    notification.className = `alert alert-${type} alert-dismissible fade show mb-2`;
 
     notification.innerHTML = `
         ${message}
         <button type="button" class="btn-close" data-bs-dismiss="alert"></button>
     `;
 
-    document.body.appendChild(notification);
+    container.appendChild(notification);
 
     // Auto-remove after 5 seconds
     setTimeout(() => {

app/web/templates/setup.html

@@ -0,0 +1,60 @@
+{% extends "base.html" %}
+
+{% block title %}Setup - SneakyScanner{% endblock %}
+
+{% set hide_nav = true %}
+
+{% block content %}
+<div class="login-card">
+    <div class="text-center mb-4">
+        <h1 class="brand-title">SneakyScanner</h1>
+        <p class="brand-subtitle">Initial Setup</p>
+    </div>
+
+    <div class="alert alert-info mb-4">
+        <i class="bi bi-info-circle me-1"></i>
+        <strong>Welcome!</strong> Please set an application password to secure your scanner.
+    </div>
+
+    {% with messages = get_flashed_messages(with_categories=true) %}
+        {% if messages %}
+            {% for category, message in messages %}
+                <div class="alert alert-{{ 'danger' if category == 'error' else category }} alert-dismissible fade show" role="alert">
+                    {{ message }}
+                    <button type="button" class="btn-close" data-bs-dismiss="alert"></button>
+                </div>
+            {% endfor %}
+        {% endif %}
+    {% endwith %}
+
+    <form method="post" action="{{ url_for('auth.setup') }}">
+        <div class="mb-3">
+            <label for="password" class="form-label">Password</label>
+            <input type="password"
+                   class="form-control form-control-lg"
+                   id="password"
+                   name="password"
+                   required
+                   minlength="8"
+                   autofocus
+                   placeholder="Enter password (min 8 characters)">
+            <div class="form-text">Password must be at least 8 characters long.</div>
+        </div>
+
+        <div class="mb-4">
+            <label for="confirm_password" class="form-label">Confirm Password</label>
+            <input type="password"
+                   class="form-control form-control-lg"
+                   id="confirm_password"
+                   name="confirm_password"
+                   required
+                   minlength="8"
+                   placeholder="Confirm your password">
+        </div>
+
+        <button type="submit" class="btn btn-primary btn-lg w-100">
+            Set Password
+        </button>
+    </form>
+</div>
+{% endblock %}

app/web/templates/webhook_presets/custom_json.j2

@@ -0,0 +1,9 @@
+{
+  "title": "{{ scan.title }} - {{ alert.type|title|replace('_', ' ') }}",
+  "message": "{{ alert.message }}{% if alert.ip_address %} on {{ alert.ip_address }}{% endif %}{% if alert.port %}:{{ alert.port }}{% endif %}",
+  "priority": {% if alert.severity == 'critical' %}5{% elif alert.severity == 'warning' %}3{% else %}1{% endif %},
+  "severity": "{{ alert.severity }}",
+  "scan_id": {{ scan.id }},
+  "alert_id": {{ alert.id }},
+  "timestamp": "{{ timestamp.isoformat() }}"
+}

app/web/templates/webhook_presets/default_json.j2

@@ -0,0 +1,25 @@
+{
+  "event": "alert.created",
+  "alert": {
+    "id": {{ alert.id }},
+    "type": "{{ alert.type }}",
+    "severity": "{{ alert.severity }}",
+    "message": "{{ alert.message }}",
+    {% if alert.ip_address %}"ip_address": "{{ alert.ip_address }}",{% endif %}
+    {% if alert.port %}"port": {{ alert.port }},{% endif %}
+    "acknowledged": {{ alert.acknowledged|lower }},
+    "created_at": "{{ alert.created_at.isoformat() }}"
+  },
+  "scan": {
+    "id": {{ scan.id }},
+    "title": "{{ scan.title }}",
+    "timestamp": "{{ scan.timestamp.isoformat() }}",
+    "status": "{{ scan.status }}"
+  },
+  "rule": {
+    "id": {{ rule.id }},
+    "name": "{{ rule.name }}",
+    "type": "{{ rule.type }}",
+    "threshold": {{ rule.threshold if rule.threshold else 'null' }}
+  }
+}