added webhooks and templates to alerting, email is next

.env.example

@@ -28,9 +28,10 @@ DATABASE_URL=sqlite:////app/data/sneakyscanner.db
 SECRET_KEY=your-secret-key-here-change-in-production
 
 # SNEAKYSCANNER_ENCRYPTION_KEY: Used for encrypting sensitive settings in database
-# IMPORTANT: Change this to a random string in production!
+# IMPORTANT: Must be a valid Fernet key (32 url-safe base64-encoded bytes)
 # Generate with: python3 -c "from cryptography.fernet import Fernet; print(Fernet.generate_key().decode())"
-SNEAKYSCANNER_ENCRYPTION_KEY=your-encryption-key-here
+# Example: N3RhbGx5VmFsaWRGZXJuZXRLZXlIZXJlMTIzNDU2Nzg5MA==
+SNEAKYSCANNER_ENCRYPTION_KEY=
 
 # ================================
 # CORS Configuration
@@ -57,8 +58,10 @@ SCHEDULER_EXECUTORS=2
 SCHEDULER_JOB_DEFAULTS_MAX_INSTANCES=3
 
 # ================================
-# Optional: Application Password
+# Initial Password (First Run)
 # ================================
-# If you want to set the application password via environment variable
-# Otherwise, set it via init_db.py --password
-# APP_PASSWORD=your-password-here
+# Password used for database initialization on first run
+# This will be set as the application login password
+# Leave blank to auto-generate a random password (saved to ./logs/admin_password.txt)
+# IMPORTANT: Change this after first login!
+INITIAL_PASSWORD=

.gitignore

@@ -9,6 +9,11 @@ output/
 data/
 logs/
 
+# Environment and secrets
+.env
+admin_password.txt
+logs/admin_password.txt
+
 # Python
 __pycache__/
 *.py[cod]

Dockerfile

@@ -39,12 +39,13 @@ 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

README.md

@@ -28,6 +28,28 @@ A comprehensive network scanning and infrastructure monitoring platform with web
 
 ### Web Application (Recommended)
 
+**Easy Setup (One Command):**
+
+```bash
+# 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>
@@ -35,16 +57,12 @@ cd SneakyScan
 
 # 2. Configure environment
 cp .env.example .env
-# Edit .env and set SECRET_KEY and SNEAKYSCANNER_ENCRYPTION_KEY
+# Edit .env and set SECRET_KEY, SNEAKYSCANNER_ENCRYPTION_KEY, and INITIAL_PASSWORD
 
-# 3. Build and start
-docker compose build
-docker compose up -d
+# 3. Build and start (database auto-initializes on first run)
+docker compose up --build -d
 
-# 4. Initialize database
-docker compose run --rm init-db --password "YourSecurePassword"
-
-# 5. Access web interface
+# 4. Access web interface
 # Open http://localhost:5000
 ```
 

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_file': 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_file': 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_file': 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_file': 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_file': 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_file=rule_data['config_file'],
+                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/requirements-web.txt

@@ -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/validate_phase1.py

@@ -1,197 +0,0 @@
-#!/usr/bin/env python3
-"""
-Phase 1 validation script.
-
-Validates that all Phase 1 deliverables are in place and code structure is correct.
-Does not require dependencies to be installed.
-"""
-
-import ast
-import os
-import sys
-from pathlib import Path
-
-
-def validate_file_exists(file_path, description):
-    """Check if a file exists."""
-    if Path(file_path).exists():
-        print(f"✓ {description}: {file_path}")
-        return True
-    else:
-        print(f"✗ {description} missing: {file_path}")
-        return False
-
-
-def validate_directory_exists(dir_path, description):
-    """Check if a directory exists."""
-    if Path(dir_path).is_dir():
-        print(f"✓ {description}: {dir_path}")
-        return True
-    else:
-        print(f"✗ {description} missing: {dir_path}")
-        return False
-
-
-def validate_python_syntax(file_path):
-    """Validate Python file syntax."""
-    try:
-        with open(file_path, 'r') as f:
-            ast.parse(f.read())
-        return True
-    except SyntaxError as e:
-        print(f"  ✗ Syntax error in {file_path}: {e}")
-        return False
-
-
-def main():
-    """Run all validation checks."""
-    print("=" * 70)
-    print("SneakyScanner Phase 1 Validation")
-    print("=" * 70)
-
-    all_passed = True
-
-    # Check project structure
-    print("\n1. Project Structure:")
-    print("-" * 70)
-
-    structure_checks = [
-        ("web/", "Web application directory"),
-        ("web/api/", "API blueprints directory"),
-        ("web/templates/", "Jinja2 templates directory"),
-        ("web/static/", "Static files directory"),
-        ("web/utils/", "Utility modules directory"),
-        ("migrations/", "Alembic migrations directory"),
-        ("migrations/versions/", "Migration versions directory"),
-    ]
-
-    for path, desc in structure_checks:
-        if not validate_directory_exists(path, desc):
-            all_passed = False
-
-    # Check core files
-    print("\n2. Core Files:")
-    print("-" * 70)
-
-    core_files = [
-        ("requirements-web.txt", "Web dependencies"),
-        ("alembic.ini", "Alembic configuration"),
-        ("init_db.py", "Database initialization script"),
-        ("docker-compose-web.yml", "Docker Compose for web app"),
-    ]
-
-    for path, desc in core_files:
-        if not validate_file_exists(path, desc):
-            all_passed = False
-
-    # Check Python modules
-    print("\n3. Python Modules:")
-    print("-" * 70)
-
-    python_modules = [
-        ("web/__init__.py", "Web package init"),
-        ("web/models.py", "SQLAlchemy models"),
-        ("web/app.py", "Flask application factory"),
-        ("web/utils/__init__.py", "Utils package init"),
-        ("web/utils/settings.py", "Settings manager"),
-        ("web/api/__init__.py", "API package init"),
-        ("web/api/scans.py", "Scans API blueprint"),
-        ("web/api/schedules.py", "Schedules API blueprint"),
-        ("web/api/alerts.py", "Alerts API blueprint"),
-        ("web/api/settings.py", "Settings API blueprint"),
-        ("migrations/env.py", "Alembic environment"),
-        ("migrations/script.py.mako", "Migration template"),
-        ("migrations/versions/001_initial_schema.py", "Initial migration"),
-    ]
-
-    for path, desc in python_modules:
-        exists = validate_file_exists(path, desc)
-        if exists:
-            # Skip syntax check for .mako templates (they're not pure Python)
-            if not path.endswith('.mako'):
-                if not validate_python_syntax(path):
-                    all_passed = False
-            else:
-                print(f"  (Skipped syntax check for template file)")
-        else:
-            all_passed = False
-
-    # Check models
-    print("\n4. Database Models (from models.py):")
-    print("-" * 70)
-
-    try:
-        # Read models.py and look for class definitions
-        with open('web/models.py', 'r') as f:
-            content = f.read()
-            tree = ast.parse(content)
-
-        models = []
-        for node in ast.walk(tree):
-            if isinstance(node, ast.ClassDef) and node.name != 'Base':
-                models.append(node.name)
-
-        expected_models = [
-            'Scan', 'ScanSite', 'ScanIP', 'ScanPort', 'ScanService',
-            'ScanCertificate', 'ScanTLSVersion', 'Schedule', 'Alert',
-            'AlertRule', 'Setting'
-        ]
-
-        for model in expected_models:
-            if model in models:
-                print(f"✓ Model defined: {model}")
-            else:
-                print(f"✗ Model missing: {model}")
-                all_passed = False
-
-    except Exception as e:
-        print(f"✗ Failed to parse models.py: {e}")
-        all_passed = False
-
-    # Check API endpoints
-    print("\n5. API Blueprints:")
-    print("-" * 70)
-
-    blueprints = {
-        'web/api/scans.py': ['list_scans', 'get_scan', 'trigger_scan', 'delete_scan'],
-        'web/api/schedules.py': ['list_schedules', 'get_schedule', 'create_schedule'],
-        'web/api/alerts.py': ['list_alerts', 'list_alert_rules'],
-        'web/api/settings.py': ['get_settings', 'update_settings'],
-    }
-
-    for blueprint_file, expected_funcs in blueprints.items():
-        try:
-            with open(blueprint_file, 'r') as f:
-                content = f.read()
-                tree = ast.parse(content)
-
-            functions = [node.name for node in ast.walk(tree) if isinstance(node, ast.FunctionDef)]
-
-            print(f"\n  {blueprint_file}:")
-            for func in expected_funcs:
-                if func in functions:
-                    print(f"    ✓ Endpoint: {func}")
-                else:
-                    print(f"    ✗ Missing endpoint: {func}")
-                    all_passed = False
-        except Exception as e:
-            print(f"  ✗ Failed to parse {blueprint_file}: {e}")
-            all_passed = False
-
-    # Summary
-    print("\n" + "=" * 70)
-    if all_passed:
-        print("✓ All Phase 1 validation checks passed!")
-        print("\nNext steps:")
-        print("1. Install dependencies: pip install -r requirements-web.txt")
-        print("2. Initialize database: python3 init_db.py --password YOUR_PASSWORD")
-        print("3. Run Flask app: python3 -m web.app")
-        print("4. Test API: curl http://localhost:5000/api/settings/health")
-        return 0
-    else:
-        print("✗ Some validation checks failed. Please review errors above.")
-        return 1
-
-
-if __name__ == '__main__':
-    sys.exit(main())

app/web/api/alerts.py

@@ -4,9 +4,13 @@ Alerts API blueprint.
 Handles endpoints for viewing alert history and managing alert rules.
 """
 
-from flask import Blueprint, jsonify, request
+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__)
 
@@ -22,22 +26,126 @@ def list_alerts():
         per_page: Items per page (default: 20)
         alert_type: Filter by alert type
         severity: Filter by severity (info, warning, critical)
-        start_date: Filter alerts after this date
-        end_date: Filter alerts before this date
+        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
     """
-    # TODO: Implement in Phase 4
+    # 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': [],
-        'total': 0,
-        'page': 1,
-        'per_page': 20,
-        'message': 'Alerts list endpoint - to be implemented in Phase 4'
+        '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('/rules', methods=['GET'])
 @api_auth_required
 def list_alert_rules():
@@ -47,10 +155,28 @@ def list_alert_rules():
     Returns:
         JSON response with alert rules
     """
-    # TODO: Implement in Phase 4
+    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_file': rule.config_file,
+            'created_at': rule.created_at.isoformat(),
+            'updated_at': rule.updated_at.isoformat() if rule.updated_at else None
+        })
+
     return jsonify({
-        'rules': [],
-        'message': 'Alert rules list endpoint - to be implemented in Phase 4'
+        'rules': rules_data,
+        'total': len(rules_data)
     })
 
 
@@ -61,23 +187,88 @@ def create_alert_rule():
     Create a new alert rule.
 
     Request body:
-        rule_type: Type of alert rule
-        threshold: Threshold value (e.g., days for cert expiry)
+        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_file: Optional config file to apply rule to
 
     Returns:
-        JSON response with created rule ID
+        JSON response with created rule
     """
-    # TODO: Implement in Phase 4
     data = request.get_json() or {}
 
-    return jsonify({
-        'rule_id': None,
-        'status': 'not_implemented',
-        'message': 'Alert rule creation endpoint - to be implemented in Phase 4',
-        'data': data
-    }), 501
+    # 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:
+        # 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_file=data.get('config_file'),
+            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_file': rule.config_file,
+                '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'])
@@ -90,22 +281,84 @@ def update_alert_rule(rule_id):
         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_file: Config file to apply rule to (optional)
 
     Returns:
         JSON response with update status
     """
-    # TODO: Implement in Phase 4
     data = request.get_json() or {}
 
-    return jsonify({
-        'rule_id': rule_id,
-        'status': 'not_implemented',
-        'message': 'Alert rule update endpoint - to be implemented in Phase 4',
-        'data': data
-    }), 501
+    # 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:
+        # 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_file' in data:
+            rule.config_file = data['config_file']
+
+        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_file': rule.config_file,
+                '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'])
@@ -120,12 +373,83 @@ def delete_alert_rule(rule_id):
     Returns:
         JSON response with deletion status
     """
-    # TODO: Implement in Phase 4
+    # 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({
-        'rule_id': rule_id,
-        'status': 'not_implemented',
-        'message': 'Alert rule deletion endpoint - to be implemented in Phase 4'
-    }), 501
+        '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
@@ -140,5 +464,5 @@ def health_check():
     return jsonify({
         'status': 'healthy',
         'api': 'alerts',
-        'version': '1.0.0-phase1'
+        'version': '1.0.0-phase5'
     })

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/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

@@ -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)
 
@@ -328,11 +331,13 @@ 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.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')
@@ -340,10 +345,14 @@ 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')
@@ -487,6 +496,35 @@ 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 +1,13 @@
+"""
+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-phase5'
+
+# Repository URL
+REPO_URL = 'https://git.sneakygeek.net/sneakygeek/SneakyScan'

app/web/jobs/scan_job.py

@@ -16,6 +16,7 @@ from sqlalchemy.orm import sessionmaker
 from src.scanner import SneakyScanner
 from web.models import Scan
 from web.services.scan_service import ScanService
+from web.services.alert_service import AlertService
 
 logger = logging.getLogger(__name__)
 
@@ -89,6 +90,17 @@ def execute_scan(scan_id: int, config_file: str, db_url: str):
         scan_service = ScanService(session)
         scan_service._save_scan_to_db(report, scan_id, status='completed')
 
+        # 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 FileNotFoundError as e:

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

@@ -284,17 +284,24 @@ 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 +322,82 @@ 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_file = Column(String(255), nullable=True, comment="Optional: specific config file 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")
 
     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

@@ -219,3 +219,105 @@ def edit_config(filename):
         logger.error(f"Error loading config for edit: {e}")
         flash(f"Error loading config: {str(e)}", 'error')
         return redirect(url_for('main.configs'))
+
+
+@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
+    """
+    import os
+    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 = []
+
+    # Get list of available config files
+    configs_dir = '/app/configs'
+    config_files = []
+
+    try:
+        if os.path.exists(configs_dir):
+            config_files = [f for f in os.listdir(configs_dir) if f.endswith(('.yaml', '.yml'))]
+            config_files.sort()
+    except Exception as e:
+        logger.error(f"Error listing config files: {e}")
+
+    return render_template(
+        'alert_rules.html',
+        rules=rules,
+        config_files=config_files
+    )

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_file and scan.config_file != rule.config_file:
+                    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_file
+        previous_scan = (
+            self.db.query(Scan)
+            .filter(Scan.config_file == scan.config_file)
+            .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 {scan.config_file}")
+            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/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_file": scan.config_file,
+                "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_file": "production-scan.yaml",
+                "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/templates/alert_rules.html

@@ -0,0 +1,474 @@
+{% 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 style="color: #60a5fa;">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" style="color: #60a5fa;">{{ 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" style="color: #60a5fa;">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_file %}
+                                        <small class="text-muted">{{ rule.config_file }}</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">Active</span>
+                                            {% else %}
+                                                <span class="text-muted">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>
+                                {% if config_files %}
+                                    {% for config_file in config_files %}
+                                    <option value="{{ config_file }}">{{ config_file }}</option>
+                                    {% endfor %}
+                                {% else %}
+                                    <option value="" disabled>No config files found</option>
+                                {% endif %}
+                            </select>
+                            <small class="form-text text-muted">
+                                {% if config_files %}
+                                    Select a specific config file to limit this rule, or leave as "All Configs" to apply to all scans
+                                {% else %}
+                                    No config files found. Upload a config in the Configs section to see available options.
+                                {% endif %}
+                            </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;
+
+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;
+    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';
+
+    // 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_file || '';
+            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 configFile = 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_file: configFile || 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 +1,269 @@
+{% 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 style="color: #60a5fa;">Alert History</h1>
+        <a href="{{ url_for('main.alert_rules') }}" class="btn btn-primary">
+            <i class="bi bi-gear"></i> Manage Alert Rules
+        </a>
+    </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" style="color: #60a5fa;">{{ 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" style="color: #f97316;">
+                    {{ 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" style="color: #60a5fa;">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');
+    });
+}
+</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>
@@ -57,6 +57,18 @@
                         <a class="nav-link {% if request.endpoint and 'config' in request.endpoint %}active{% endif %}"
                            href="{{ url_for('main.configs') }}">Configs</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>
                 <ul class="navbar-nav">
                     <li class="nav-item">
@@ -85,7 +97,7 @@
 
     <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>
 

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' }}
+  }
+}

app/web/templates/webhook_presets/discord.j2

@@ -0,0 +1,41 @@
+{
+  "username": "SneakyScanner",
+  "embeds": [
+    {
+      "title": "{{ alert.type|title|replace('_', ' ') }} Alert",
+      "description": "{{ alert.message }}",
+      "color": {% if alert.severity == 'critical' %}15158332{% elif alert.severity == 'warning' %}16776960{% else %}3447003{% endif %},
+      "fields": [
+        {
+          "name": "Severity",
+          "value": "{{ alert.severity|upper }}",
+          "inline": true
+        },
+        {
+          "name": "Scan",
+          "value": "{{ scan.title }}",
+          "inline": true
+        },
+        {
+          "name": "Rule",
+          "value": "{{ rule.name }}",
+          "inline": false
+        }{% if alert.ip_address %},
+        {
+          "name": "IP Address",
+          "value": "{{ alert.ip_address }}",
+          "inline": true
+        }{% endif %}{% if alert.port %},
+        {
+          "name": "Port",
+          "value": "{{ alert.port }}",
+          "inline": true
+        }{% endif %}
+      ],
+      "footer": {
+        "text": "Alert ID: {{ alert.id }} | Scan ID: {{ scan.id }}"
+      },
+      "timestamp": "{{ timestamp.isoformat() }}"
+    }
+  ]
+}

app/web/templates/webhook_presets/gotify.j2

@@ -0,0 +1,13 @@
+{
+  "title": "{{ scan.title }}",
+  "message": "**{{ alert.severity|upper }}**: {{ alert.message }}\n\n**Scan:** {{ scan.title }}\n**Status:** {{ scan.status }}\n**Rule:** {{ rule.name }}{% if alert.ip_address %}\n**IP:** {{ alert.ip_address }}{% endif %}{% if alert.port %}\n**Port:** {{ alert.port }}{% endif %}",
+  "priority": {% if alert.severity == 'critical' %}8{% elif alert.severity == 'warning' %}5{% else %}2{% endif %},
+  "extras": {
+    "client::display": {
+      "contentType": "text/markdown"
+    },
+    "alert_id": {{ alert.id }},
+    "scan_id": {{ scan.id }},
+    "alert_type": "{{ alert.type }}"
+  }
+}

app/web/templates/webhook_presets/ntfy.j2

@@ -0,0 +1,10 @@
+{{ alert.message }}
+
+Scan: {{ scan.title }}
+Rule: {{ rule.name }}
+Severity: {{ alert.severity|upper }}{% if alert.ip_address %}
+IP: {{ alert.ip_address }}{% endif %}{% if alert.port %}
+Port: {{ alert.port }}{% endif %}
+
+Scan Status: {{ scan.status }}
+Alert ID: {{ alert.id }}

app/web/templates/webhook_presets/plain_text.j2

@@ -0,0 +1,27 @@
+SNEAKYSCANNER ALERT - {{ alert.severity|upper }}
+
+Alert: {{ alert.message }}
+Type: {{ alert.type|title|replace('_', ' ') }}
+Severity: {{ alert.severity|upper }}
+
+Scan Information:
+  Title: {{ scan.title }}
+  Status: {{ scan.status }}
+  Duration: {{ scan.duration }}s
+  Triggered By: {{ scan.triggered_by }}
+
+Rule Information:
+  Name: {{ rule.name }}
+  Type: {{ rule.type }}
+{% if rule.threshold %}  Threshold: {{ rule.threshold }}
+{% endif %}
+{% if alert.ip_address %}IP Address: {{ alert.ip_address }}
+{% endif %}{% if alert.port %}Port: {{ alert.port }}
+{% endif %}
+Alert ID: {{ alert.id }}
+Scan ID: {{ scan.id }}
+Timestamp: {{ timestamp.strftime('%Y-%m-%d %H:%M:%S UTC') }}
+
+---
+Generated by {{ app.name }} v{{ app.version }}
+{{ app.url }}

app/web/templates/webhook_presets/presets.json

@@ -0,0 +1,65 @@
+[
+  {
+    "id": "default_json",
+    "name": "Default JSON (Current Format)",
+    "description": "Standard webhook payload format matching the current implementation",
+    "format": "json",
+    "content_type": "application/json",
+    "file": "default_json.j2",
+    "category": "general"
+  },
+  {
+    "id": "custom_json",
+    "name": "Custom JSON",
+    "description": "Flexible custom JSON format with configurable title, message, and priority fields",
+    "format": "json",
+    "content_type": "application/json",
+    "file": "custom_json.j2",
+    "category": "general"
+  },
+  {
+    "id": "gotify",
+    "name": "Gotify",
+    "description": "Optimized for Gotify push notification server with markdown support",
+    "format": "json",
+    "content_type": "application/json",
+    "file": "gotify.j2",
+    "category": "service"
+  },
+  {
+    "id": "ntfy",
+    "name": "Ntfy",
+    "description": "Simple text format for Ntfy pub-sub notification service",
+    "format": "text",
+    "content_type": "text/plain",
+    "file": "ntfy.j2",
+    "category": "service"
+  },
+  {
+    "id": "slack",
+    "name": "Slack",
+    "description": "Rich Block Kit format for Slack webhooks with visual formatting",
+    "format": "json",
+    "content_type": "application/json",
+    "file": "slack.j2",
+    "category": "service"
+  },
+  {
+    "id": "discord",
+    "name": "Discord",
+    "description": "Embedded message format for Discord webhooks with color-coded severity",
+    "format": "json",
+    "content_type": "application/json",
+    "file": "discord.j2",
+    "category": "service"
+  },
+  {
+    "id": "plain_text",
+    "name": "Plain Text",
+    "description": "Simple plain text format for logging or basic notification services",
+    "format": "text",
+    "content_type": "text/plain",
+    "file": "plain_text.j2",
+    "category": "general"
+  }
+]

app/web/templates/webhook_presets/slack.j2

@@ -0,0 +1,60 @@
+{
+  "text": "{{ alert.severity|upper }}: {{ alert.message }}",
+  "blocks": [
+    {
+      "type": "header",
+      "text": {
+        "type": "plain_text",
+        "text": "🚨 {{ alert.severity|upper }} Alert: {{ alert.type|title|replace('_', ' ') }}"
+      }
+    },
+    {
+      "type": "section",
+      "fields": [
+        {
+          "type": "mrkdwn",
+          "text": "*Alert:*\n{{ alert.message }}"
+        },
+        {
+          "type": "mrkdwn",
+          "text": "*Severity:*\n{{ alert.severity|upper }}"
+        }
+      ]
+    },
+    {
+      "type": "section",
+      "fields": [
+        {
+          "type": "mrkdwn",
+          "text": "*Scan:*\n{{ scan.title }}"
+        },
+        {
+          "type": "mrkdwn",
+          "text": "*Rule:*\n{{ rule.name }}"
+        }
+      ]
+    }{% if alert.ip_address or alert.port %},
+    {
+      "type": "section",
+      "fields": [{% if alert.ip_address %}
+        {
+          "type": "mrkdwn",
+          "text": "*IP Address:*\n{{ alert.ip_address }}"
+        }{% if alert.port %},{% endif %}{% endif %}{% if alert.port %}
+        {
+          "type": "mrkdwn",
+          "text": "*Port:*\n{{ alert.port }}"
+        }{% endif %}
+      ]
+    }{% endif %},
+    {
+      "type": "context",
+      "elements": [
+        {
+          "type": "mrkdwn",
+          "text": "Scan ID: {{ scan.id }} | Alert ID: {{ alert.id }} | {{ timestamp.strftime('%Y-%m-%d %H:%M:%S UTC') }}"
+        }
+      ]
+    }
+  ]
+}

app/web/templates/webhooks/form.html

@@ -0,0 +1,633 @@
+{% extends "base.html" %}
+
+{% block title %}{{ 'Edit' if mode == 'edit' else 'New' }} Webhook - SneakyScanner{% endblock %}
+
+{% block content %}
+<div class="row mt-4">
+    <div class="col-12 mb-4">
+        <h1 style="color: #60a5fa;">{{ 'Edit' if mode == 'edit' else 'Create' }} Webhook</h1>
+        <nav aria-label="breadcrumb">
+            <ol class="breadcrumb">
+                <li class="breadcrumb-item"><a href="{{ url_for('webhooks.list_webhooks') }}">Webhooks</a></li>
+                <li class="breadcrumb-item active">{{ 'Edit' if mode == 'edit' else 'New' }}</li>
+            </ol>
+        </nav>
+    </div>
+</div>
+
+<div class="row">
+    <div class="col-lg-8">
+        <div class="card">
+            <div class="card-body">
+                <form id="webhook-form">
+                    <!-- Basic Information -->
+                    <h5 class="card-title mb-3">Basic Information</h5>
+
+                    <div class="mb-3">
+                        <label for="name" class="form-label">Webhook Name <span class="text-danger">*</span></label>
+                        <input type="text" class="form-control" id="name" name="name" required
+                            placeholder="e.g., Slack Notifications">
+                        <div class="form-text">A descriptive name for this webhook</div>
+                    </div>
+
+                    <div class="mb-3">
+                        <label for="url" class="form-label">Webhook URL <span class="text-danger">*</span></label>
+                        <input type="url" class="form-control" id="url" name="url" required
+                            placeholder="https://hooks.example.com/webhook">
+                        <div class="form-text">The endpoint where alerts will be sent</div>
+                    </div>
+
+                    <div class="mb-3">
+                        <div class="form-check form-switch">
+                            <input class="form-check-input" type="checkbox" id="enabled" name="enabled" checked>
+                            <label class="form-check-label" for="enabled">Enabled</label>
+                        </div>
+                        <div class="form-text">Disabled webhooks will not receive notifications</div>
+                    </div>
+
+                    <hr class="my-4">
+
+                    <!-- Authentication -->
+                    <h5 class="card-title mb-3">Authentication</h5>
+
+                    <div class="mb-3">
+                        <label for="auth_type" class="form-label">Authentication Type</label>
+                        <select class="form-select" id="auth_type" name="auth_type">
+                            <option value="none">None</option>
+                            <option value="bearer">Bearer Token</option>
+                            <option value="basic">Basic Auth (username:password)</option>
+                            <option value="custom">Custom Headers</option>
+                        </select>
+                    </div>
+
+                    <div class="mb-3" id="auth_token_field" style="display: none;">
+                        <label for="auth_token" class="form-label">Authentication Token</label>
+                        <input type="password" class="form-control" id="auth_token" name="auth_token"
+                            placeholder="Enter token or username:password">
+                        <div class="form-text" id="auth_token_help">Will be encrypted when stored</div>
+                    </div>
+
+                    <div class="mb-3" id="custom_headers_field" style="display: none;">
+                        <label for="custom_headers" class="form-label">Custom Headers (JSON)</label>
+                        <textarea class="form-control font-monospace" id="custom_headers" name="custom_headers" rows="4"
+                            placeholder='{"X-API-Key": "your-key", "X-Custom-Header": "value"}'></textarea>
+                        <div class="form-text">JSON object with custom HTTP headers</div>
+                    </div>
+
+                    <hr class="my-4">
+
+                    <!-- Filters -->
+                    <h5 class="card-title mb-3">Alert Filters</h5>
+
+                    <div class="mb-3">
+                        <label class="form-label">Alert Types</label>
+                        <div class="form-text mb-2">Select which alert types trigger this webhook (leave all unchecked for all types)</div>
+                        <div class="form-check">
+                            <input class="form-check-input alert-type-check" type="checkbox" value="unexpected_port" id="type_unexpected">
+                            <label class="form-check-label" for="type_unexpected">Unexpected Port</label>
+                        </div>
+                        <div class="form-check">
+                            <input class="form-check-input alert-type-check" type="checkbox" value="drift_detection" id="type_drift">
+                            <label class="form-check-label" for="type_drift">Drift Detection</label>
+                        </div>
+                        <div class="form-check">
+                            <input class="form-check-input alert-type-check" type="checkbox" value="cert_expiry" id="type_cert">
+                            <label class="form-check-label" for="type_cert">Certificate Expiry</label>
+                        </div>
+                        <div class="form-check">
+                            <input class="form-check-input alert-type-check" type="checkbox" value="weak_tls" id="type_tls">
+                            <label class="form-check-label" for="type_tls">Weak TLS</label>
+                        </div>
+                        <div class="form-check">
+                            <input class="form-check-input alert-type-check" type="checkbox" value="ping_failed" id="type_ping">
+                            <label class="form-check-label" for="type_ping">Ping Failed</label>
+                        </div>
+                    </div>
+
+                    <div class="mb-3">
+                        <label class="form-label">Severity Filter</label>
+                        <div class="form-text mb-2">Select which severities trigger this webhook (leave all unchecked for all severities)</div>
+                        <div class="form-check">
+                            <input class="form-check-input severity-check" type="checkbox" value="critical" id="severity_critical">
+                            <label class="form-check-label" for="severity_critical">Critical</label>
+                        </div>
+                        <div class="form-check">
+                            <input class="form-check-input severity-check" type="checkbox" value="warning" id="severity_warning">
+                            <label class="form-check-label" for="severity_warning">Warning</label>
+                        </div>
+                        <div class="form-check">
+                            <input class="form-check-input severity-check" type="checkbox" value="info" id="severity_info">
+                            <label class="form-check-label" for="severity_info">Info</label>
+                        </div>
+                    </div>
+
+                    <hr class="my-4">
+
+                    <!-- Webhook Template -->
+                    <h5 class="card-title mb-3">Webhook Template</h5>
+                    <div class="alert alert-info small">
+                        <i class="bi bi-info-circle"></i>
+                        Customize the webhook payload using Jinja2 templates. Leave empty to use the default JSON format.
+                    </div>
+
+                    <div class="mb-3">
+                        <label for="preset_selector" class="form-label">Load Preset Template</label>
+                        <select class="form-select" id="preset_selector">
+                            <option value="">-- Select a preset --</option>
+                        </select>
+                        <div class="form-text">Choose from pre-built templates for popular services</div>
+                    </div>
+
+                    <div class="mb-3">
+                        <label for="template_format" class="form-label">Template Format</label>
+                        <select class="form-select" id="template_format" name="template_format">
+                            <option value="json">JSON</option>
+                            <option value="text">Plain Text</option>
+                        </select>
+                        <div class="form-text">Output format of the rendered template</div>
+                    </div>
+
+                    <div class="mb-3">
+                        <label for="template" class="form-label">Template</label>
+                        <textarea class="form-control font-monospace" id="template" name="template" rows="12"
+                            placeholder="Leave empty for default format, or enter custom Jinja2 template..."></textarea>
+                        <div class="form-text">
+                            Available variables: <code>{{ "{{" }} alert.* {{ "}}" }}</code>, <code>{{ "{{" }} scan.* {{ "}}" }}</code>, <code>{{ "{{" }} rule.* {{ "}}" }}</code>
+                            <a href="#" data-bs-toggle="modal" data-bs-target="#variablesModal">View all variables</a>
+                        </div>
+                    </div>
+
+                    <div class="mb-3">
+                        <label for="content_type_override" class="form-label">Custom Content-Type (optional)</label>
+                        <input type="text" class="form-control font-monospace" id="content_type_override" name="content_type_override"
+                            placeholder="e.g., application/json, text/plain, text/markdown">
+                        <div class="form-text">Override the default Content-Type header (auto-detected from template format if not set)</div>
+                    </div>
+
+                    <div class="mb-3">
+                        <button type="button" class="btn btn-outline-secondary btn-sm" id="preview-template-btn">
+                            <i class="bi bi-eye"></i> Preview Template
+                        </button>
+                        <button type="button" class="btn btn-outline-secondary btn-sm ms-2" id="clear-template-btn">
+                            <i class="bi bi-x-circle"></i> Clear Template
+                        </button>
+                    </div>
+
+                    <hr class="my-4">
+
+                    <!-- Advanced Settings -->
+                    <h5 class="card-title mb-3">Advanced Settings</h5>
+
+                    <div class="row">
+                        <div class="col-md-6 mb-3">
+                            <label for="timeout" class="form-label">Timeout (seconds)</label>
+                            <input type="number" class="form-control" id="timeout" name="timeout" min="1" max="60" value="10">
+                            <div class="form-text">Maximum time to wait for response</div>
+                        </div>
+
+                        <div class="col-md-6 mb-3">
+                            <label for="retry_count" class="form-label">Retry Count</label>
+                            <input type="number" class="form-control" id="retry_count" name="retry_count" min="0" max="5" value="3">
+                            <div class="form-text">Number of retry attempts on failure</div>
+                        </div>
+                    </div>
+
+                    <hr class="my-4">
+
+                    <!-- Submit Buttons -->
+                    <div class="d-flex justify-content-between">
+                        <a href="{{ url_for('webhooks.list_webhooks') }}" class="btn btn-secondary">Cancel</a>
+                        <div>
+                            <button type="button" class="btn btn-outline-primary me-2" id="test-btn">
+                                <i class="bi bi-send"></i> Test Webhook
+                            </button>
+                            <button type="submit" class="btn btn-primary">
+                                <i class="bi bi-check-circle"></i> Save Webhook
+                            </button>
+                        </div>
+                    </div>
+                </form>
+            </div>
+        </div>
+    </div>
+
+    <!-- Help Sidebar -->
+    <div class="col-lg-4">
+        <div class="card">
+            <div class="card-body">
+                <h5 class="card-title"><i class="bi bi-info-circle"></i> Help</h5>
+
+                <h6 class="mt-3">Payload Format</h6>
+                <p class="small text-muted">Default JSON payload format (can be customized with templates):</p>
+                <pre class="small bg-dark text-light p-2 rounded"><code>{
+  "event": "alert.created",
+  "alert": {
+    "id": 123,
+    "type": "cert_expiry",
+    "severity": "warning",
+    "message": "...",
+    "ip_address": "192.168.1.10",
+    "port": 443
+  },
+  "scan": {...},
+  "rule": {...}
+}</code></pre>
+
+                <h6 class="mt-3">Custom Templates</h6>
+                <p class="small text-muted">Use Jinja2 templates to customize payloads for services like Slack, Discord, Gotify, or create your own format. Select a preset or write a custom template.</p>
+
+                <h6 class="mt-3">Authentication Types</h6>
+                <ul class="small">
+                    <li><strong>None:</strong> No authentication</li>
+                    <li><strong>Bearer:</strong> Add Authorization header with token</li>
+                    <li><strong>Basic:</strong> Use username:password format</li>
+                    <li><strong>Custom:</strong> Define custom HTTP headers</li>
+                </ul>
+
+                <h6 class="mt-3">Retry Logic</h6>
+                <p class="small text-muted">Failed webhooks are retried with exponential backoff (2^attempt seconds, max 60s).</p>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Template Variables Modal -->
+<div class="modal fade" id="variablesModal" tabindex="-1">
+    <div class="modal-dialog modal-lg">
+        <div class="modal-content">
+            <div class="modal-header">
+                <h5 class="modal-title">Available Template Variables</h5>
+                <button type="button" class="btn-close" data-bs-dismiss="modal"></button>
+            </div>
+            <div class="modal-body">
+                <h6>Alert Variables</h6>
+                <ul class="small font-monospace">
+                    <li>{{ "{{" }} alert.id {{ "}}" }} - Alert ID</li>
+                    <li>{{ "{{" }} alert.type {{ "}}" }} - Alert type (unexpected_port, cert_expiry, etc.)</li>
+                    <li>{{ "{{" }} alert.severity {{ "}}" }} - Severity level (critical, warning, info)</li>
+                    <li>{{ "{{" }} alert.message {{ "}}" }} - Human-readable alert message</li>
+                    <li>{{ "{{" }} alert.ip_address {{ "}}" }} - IP address (if applicable)</li>
+                    <li>{{ "{{" }} alert.port {{ "}}" }} - Port number (if applicable)</li>
+                    <li>{{ "{{" }} alert.acknowledged {{ "}}" }} - Boolean: is acknowledged</li>
+                    <li>{{ "{{" }} alert.created_at {{ "}}" }} - Alert creation timestamp</li>
+                </ul>
+
+                <h6 class="mt-3">Scan Variables</h6>
+                <ul class="small font-monospace">
+                    <li>{{ "{{" }} scan.id {{ "}}" }} - Scan ID</li>
+                    <li>{{ "{{" }} scan.title {{ "}}" }} - Scan title from config</li>
+                    <li>{{ "{{" }} scan.timestamp {{ "}}" }} - Scan start time</li>
+                    <li>{{ "{{" }} scan.duration {{ "}}" }} - Scan duration in seconds</li>
+                    <li>{{ "{{" }} scan.status {{ "}}" }} - Scan status (running, completed, failed)</li>
+                    <li>{{ "{{" }} scan.triggered_by {{ "}}" }} - How scan was triggered (manual, scheduled, api)</li>
+                </ul>
+
+                <h6 class="mt-3">Rule Variables</h6>
+                <ul class="small font-monospace">
+                    <li>{{ "{{" }} rule.id {{ "}}" }} - Rule ID</li>
+                    <li>{{ "{{" }} rule.name {{ "}}" }} - Rule name</li>
+                    <li>{{ "{{" }} rule.type {{ "}}" }} - Rule type</li>
+                    <li>{{ "{{" }} rule.threshold {{ "}}" }} - Rule threshold value</li>
+                    <li>{{ "{{" }} rule.severity {{ "}}" }} - Rule severity</li>
+                </ul>
+
+                <h6 class="mt-3">App Variables</h6>
+                <ul class="small font-monospace">
+                    <li>{{ "{{" }} app.name {{ "}}" }} - Application name</li>
+                    <li>{{ "{{" }} app.version {{ "}}" }} - Application version</li>
+                    <li>{{ "{{" }} app.url {{ "}}" }} - Repository URL</li>
+                </ul>
+
+                <h6 class="mt-3">Other Variables</h6>
+                <ul class="small font-monospace">
+                    <li>{{ "{{" }} timestamp {{ "}}" }} - Current UTC timestamp</li>
+                </ul>
+
+                <h6 class="mt-3">Jinja2 Features</h6>
+                <p class="small">Templates support Jinja2 syntax including:</p>
+                <ul class="small">
+                    <li>Conditionals: <code>{{ "{%" }} if alert.severity == 'critical' {{ "%}" }}...{{ "{%" }} endif {{ "%}" }}</code></li>
+                    <li>Filters: <code>{{ "{{" }} alert.type|upper {{ "}}" }}</code>, <code>{{ "{{" }} alert.created_at.isoformat() {{ "}}" }}</code></li>
+                    <li>Default values: <code>{{ "{{" }} alert.port|default('N/A') {{ "}}" }}</code></li>
+                </ul>
+            </div>
+            <div class="modal-footer">
+                <button type="button" class="btn btn-secondary" data-bs-dismiss="modal">Close</button>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Template Preview Modal -->
+<div class="modal fade" id="previewModal" tabindex="-1">
+    <div class="modal-dialog modal-lg">
+        <div class="modal-content">
+            <div class="modal-header">
+                <h5 class="modal-title">Template Preview</h5>
+                <button type="button" class="btn-close" data-bs-dismiss="modal"></button>
+            </div>
+            <div class="modal-body">
+                <p class="small text-muted">Preview using sample data:</p>
+                <pre class="bg-dark text-light p-3 rounded" id="preview-output" style="max-height: 500px; overflow-y: auto;"><code></code></pre>
+            </div>
+            <div class="modal-footer">
+                <button type="button" class="btn btn-secondary" data-bs-dismiss="modal">Close</button>
+            </div>
+        </div>
+    </div>
+</div>
+
+{% endblock %}
+
+{% block scripts %}
+<script>
+const webhookId = {{ webhook.id if webhook else 'null' }};
+const mode = '{{ mode }}';
+
+// Load template presets on page load
+async function loadPresets() {
+    try {
+        const response = await fetch('/api/webhooks/template-presets');
+        const data = await response.json();
+
+        if (data.status === 'success') {
+            const selector = document.getElementById('preset_selector');
+            data.presets.forEach(preset => {
+                const option = document.createElement('option');
+                option.value = JSON.stringify({
+                    template: preset.template,
+                    format: preset.format,
+                    content_type: preset.content_type
+                });
+                option.textContent = `${preset.name} - ${preset.description}`;
+                selector.appendChild(option);
+            });
+        }
+    } catch (error) {
+        console.error('Failed to load presets:', error);
+    }
+}
+
+// Handle preset selection
+document.getElementById('preset_selector').addEventListener('change', function() {
+    if (!this.value) return;
+
+    try {
+        const preset = JSON.parse(this.value);
+        document.getElementById('template').value = preset.template;
+        document.getElementById('template_format').value = preset.format;
+        document.getElementById('content_type_override').value = preset.content_type;
+    } catch (error) {
+        console.error('Failed to load preset:', error);
+    }
+});
+
+// Handle preview template button
+document.getElementById('preview-template-btn').addEventListener('click', async function() {
+    const template = document.getElementById('template').value.trim();
+    if (!template) {
+        alert('Please enter a template first');
+        return;
+    }
+
+    const templateFormat = document.getElementById('template_format').value;
+
+    try {
+        const response = await fetch('/api/webhooks/preview-template', {
+            method: 'POST',
+            headers: { 'Content-Type': 'application/json' },
+            body: JSON.stringify({
+                template: template,
+                template_format: templateFormat
+            })
+        });
+
+        const result = await response.json();
+
+        if (result.status === 'success') {
+            // Display preview in modal
+            const output = document.querySelector('#preview-output code');
+            if (templateFormat === 'json') {
+                // Pretty print JSON
+                try {
+                    const parsed = JSON.parse(result.rendered);
+                    output.textContent = JSON.stringify(parsed, null, 2);
+                } catch (e) {
+                    output.textContent = result.rendered;
+                }
+            } else {
+                output.textContent = result.rendered;
+            }
+
+            // Show modal
+            const modal = new bootstrap.Modal(document.getElementById('previewModal'));
+            modal.show();
+        } else {
+            alert(`Preview failed: ${result.message}`);
+        }
+    } catch (error) {
+        console.error('Error previewing template:', error);
+        alert('Failed to preview template');
+    }
+});
+
+// Handle clear template button
+document.getElementById('clear-template-btn').addEventListener('click', function() {
+    if (confirm('Clear template and reset to default format?')) {
+        document.getElementById('template').value = '';
+        document.getElementById('template_format').value = 'json';
+        document.getElementById('content_type_override').value = '';
+        document.getElementById('preset_selector').value = '';
+    }
+});
+
+// Load presets on page load
+loadPresets();
+
+// Show/hide auth fields based on type
+document.getElementById('auth_type').addEventListener('change', function() {
+    const authType = this.value;
+    const tokenField = document.getElementById('auth_token_field');
+    const headersField = document.getElementById('custom_headers_field');
+    const tokenHelp = document.getElementById('auth_token_help');
+
+    tokenField.style.display = 'none';
+    headersField.style.display = 'none';
+
+    if (authType === 'bearer') {
+        tokenField.style.display = 'block';
+        document.getElementById('auth_token').placeholder = 'Enter bearer token';
+        tokenHelp.textContent = 'Bearer token for Authorization header (encrypted when stored)';
+    } else if (authType === 'basic') {
+        tokenField.style.display = 'block';
+        document.getElementById('auth_token').placeholder = 'username:password';
+        tokenHelp.textContent = 'Format: username:password (encrypted when stored)';
+    } else if (authType === 'custom') {
+        headersField.style.display = 'block';
+    }
+});
+
+// Load existing webhook data if editing
+if (mode === 'edit' && webhookId) {
+    loadWebhookData(webhookId);
+}
+
+async function loadWebhookData(id) {
+    try {
+        const response = await fetch(`/api/webhooks/${id}`);
+        const data = await response.json();
+        const webhook = data.webhook;
+
+        // Populate form fields
+        document.getElementById('name').value = webhook.name || '';
+        document.getElementById('url').value = webhook.url || '';
+        document.getElementById('enabled').checked = webhook.enabled;
+        document.getElementById('auth_type').value = webhook.auth_type || 'none';
+        document.getElementById('timeout').value = webhook.timeout || 10;
+        document.getElementById('retry_count').value = webhook.retry_count || 3;
+
+        // Trigger auth type change to show relevant fields
+        document.getElementById('auth_type').dispatchEvent(new Event('change'));
+
+        // Don't populate auth_token (it's encrypted)
+        if (webhook.custom_headers) {
+            document.getElementById('custom_headers').value = JSON.stringify(webhook.custom_headers, null, 2);
+        }
+
+        // Check alert types
+        if (webhook.alert_types && webhook.alert_types.length > 0) {
+            webhook.alert_types.forEach(type => {
+                const checkbox = document.querySelector(`.alert-type-check[value="${type}"]`);
+                if (checkbox) checkbox.checked = true;
+            });
+        }
+
+        // Check severities
+        if (webhook.severity_filter && webhook.severity_filter.length > 0) {
+            webhook.severity_filter.forEach(sev => {
+                const checkbox = document.querySelector(`.severity-check[value="${sev}"]`);
+                if (checkbox) checkbox.checked = true;
+            });
+        }
+
+        // Load template fields
+        if (webhook.template) {
+            document.getElementById('template').value = webhook.template;
+        }
+        if (webhook.template_format) {
+            document.getElementById('template_format').value = webhook.template_format;
+        }
+        if (webhook.content_type_override) {
+            document.getElementById('content_type_override').value = webhook.content_type_override;
+        }
+    } catch (error) {
+        console.error('Error loading webhook:', error);
+        alert('Failed to load webhook data');
+    }
+}
+
+// Form submission
+document.getElementById('webhook-form').addEventListener('submit', async function(e) {
+    e.preventDefault();
+
+    const formData = {
+        name: document.getElementById('name').value,
+        url: document.getElementById('url').value,
+        enabled: document.getElementById('enabled').checked,
+        auth_type: document.getElementById('auth_type').value,
+        timeout: parseInt(document.getElementById('timeout').value),
+        retry_count: parseInt(document.getElementById('retry_count').value)
+    };
+
+    // Add auth token if provided
+    const authToken = document.getElementById('auth_token').value;
+    if (authToken) {
+        formData.auth_token = authToken;
+    }
+
+    // Add custom headers if provided
+    const customHeaders = document.getElementById('custom_headers').value;
+    if (customHeaders.trim()) {
+        try {
+            formData.custom_headers = JSON.parse(customHeaders);
+        } catch (e) {
+            alert('Invalid JSON in custom headers');
+            return;
+        }
+    }
+
+    // Collect selected alert types
+    const alertTypes = Array.from(document.querySelectorAll('.alert-type-check:checked'))
+        .map(cb => cb.value);
+    if (alertTypes.length > 0) {
+        formData.alert_types = alertTypes;
+    }
+
+    // Collect selected severities
+    const severities = Array.from(document.querySelectorAll('.severity-check:checked'))
+        .map(cb => cb.value);
+    if (severities.length > 0) {
+        formData.severity_filter = severities;
+    }
+
+    // Add template fields
+    const template = document.getElementById('template').value.trim();
+    if (template) {
+        formData.template = template;
+        formData.template_format = document.getElementById('template_format').value;
+
+        const contentTypeOverride = document.getElementById('content_type_override').value.trim();
+        if (contentTypeOverride) {
+            formData.content_type_override = contentTypeOverride;
+        }
+    }
+
+    try {
+        const url = mode === 'edit' ? `/api/webhooks/${webhookId}` : '/api/webhooks';
+        const method = mode === 'edit' ? 'PUT' : 'POST';
+
+        const response = await fetch(url, {
+            method: method,
+            headers: { 'Content-Type': 'application/json' },
+            body: JSON.stringify(formData)
+        });
+
+        const result = await response.json();
+
+        if (result.status === 'success') {
+            alert('Webhook saved successfully!');
+            window.location.href = '{{ url_for("webhooks.list_webhooks") }}';
+        } else {
+            alert(`Failed to save webhook: ${result.message}`);
+        }
+    } catch (error) {
+        console.error('Error saving webhook:', error);
+        alert('Failed to save webhook');
+    }
+});
+
+// Test webhook button
+document.getElementById('test-btn').addEventListener('click', async function() {
+    if (mode !== 'edit' || !webhookId) {
+        alert('Please save the webhook first before testing');
+        return;
+    }
+
+    if (!confirm('Send a test payload to this webhook?')) return;
+
+    try {
+        const response = await fetch(`/api/webhooks/${webhookId}/test`, { method: 'POST' });
+        const result = await response.json();
+
+        if (result.status === 'success') {
+            alert(`Test successful!\nHTTP ${result.status_code}\n${result.message}`);
+        } else {
+            alert(`Test failed:\n${result.message}`);
+        }
+    } catch (error) {
+        console.error('Error testing webhook:', error);
+        alert('Failed to test webhook');
+    }
+});
+</script>
+{% endblock %}

app/web/templates/webhooks/list.html

@@ -0,0 +1,250 @@
+{% extends "base.html" %}
+
+{% block title %}Webhooks - SneakyScanner{% endblock %}
+
+{% 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;">Webhook Management</h1>
+        <a href="{{ url_for('webhooks.new_webhook') }}" class="btn btn-primary">
+            <i class="bi bi-plus-circle"></i> Add Webhook
+        </a>
+    </div>
+</div>
+
+<!-- Loading indicator -->
+<div id="loading" class="text-center my-5">
+    <div class="spinner-border text-primary" role="status">
+        <span class="visually-hidden">Loading...</span>
+    </div>
+</div>
+
+<!-- Webhooks table -->
+<div id="webhooks-container" style="display: none;">
+    <div class="row mb-4">
+        <div class="col-12">
+            <div class="card">
+                <div class="card-body">
+                    <div class="table-responsive">
+                        <table class="table table-hover">
+                            <thead>
+                                <tr>
+                                    <th>Name</th>
+                                    <th>URL</th>
+                                    <th>Alert Types</th>
+                                    <th>Severity Filter</th>
+                                    <th>Status</th>
+                                    <th>Actions</th>
+                                </tr>
+                            </thead>
+                            <tbody id="webhooks-tbody">
+                                <!-- Populated via JavaScript -->
+                            </tbody>
+                        </table>
+                    </div>
+                </div>
+            </div>
+        </div>
+    </div>
+
+    <!-- Pagination -->
+    <nav aria-label="Webhooks pagination" id="pagination-container">
+        <ul class="pagination justify-content-center" id="pagination">
+            <!-- Populated via JavaScript -->
+        </ul>
+    </nav>
+</div>
+
+<!-- Empty state -->
+<div id="empty-state" class="text-center my-5" style="display: none;">
+    <i class="bi bi-webhook" style="font-size: 4rem; color: #94a3b8;"></i>
+    <p class="text-muted mt-3">No webhooks configured yet.</p>
+    <a href="{{ url_for('webhooks.new_webhook') }}" class="btn btn-primary">
+        <i class="bi bi-plus-circle"></i> Create Your First Webhook
+    </a>
+</div>
+
+{% endblock %}
+
+{% block scripts %}
+<script>
+let currentPage = 1;
+const perPage = 20;
+
+async function loadWebhooks(page = 1) {
+    try {
+        const response = await fetch(`/api/webhooks?page=${page}&per_page=${perPage}`);
+        const data = await response.json();
+
+        if (data.webhooks && data.webhooks.length > 0) {
+            renderWebhooks(data.webhooks);
+            renderPagination(data.page, data.pages, data.total);
+            document.getElementById('webhooks-container').style.display = 'block';
+            document.getElementById('empty-state').style.display = 'none';
+        } else {
+            document.getElementById('webhooks-container').style.display = 'none';
+            document.getElementById('empty-state').style.display = 'block';
+        }
+    } catch (error) {
+        console.error('Error loading webhooks:', error);
+        alert('Failed to load webhooks');
+    } finally {
+        document.getElementById('loading').style.display = 'none';
+    }
+}
+
+function renderWebhooks(webhooks) {
+    const tbody = document.getElementById('webhooks-tbody');
+    tbody.innerHTML = '';
+
+    webhooks.forEach(webhook => {
+        const row = document.createElement('tr');
+
+        // Truncate URL for display
+        const truncatedUrl = webhook.url.length > 50 ?
+            webhook.url.substring(0, 47) + '...' : webhook.url;
+
+        // Format alert types
+        const alertTypes = webhook.alert_types && webhook.alert_types.length > 0 ?
+            webhook.alert_types.map(t => `<span class="badge bg-secondary me-1">${t}</span>`).join('') :
+            '<span class="text-muted">All</span>';
+
+        // Format severity filter
+        const severityFilter = webhook.severity_filter && webhook.severity_filter.length > 0 ?
+            webhook.severity_filter.map(s => `<span class="badge bg-${getSeverityColor(s)} me-1">${s}</span>`).join('') :
+            '<span class="text-muted">All</span>';
+
+        // Status badge
+        const statusBadge = webhook.enabled ?
+            '<span class="badge bg-success">Enabled</span>' :
+            '<span class="badge bg-secondary">Disabled</span>';
+
+        row.innerHTML = `
+            <td><strong>${escapeHtml(webhook.name)}</strong></td>
+            <td><code class="small">${escapeHtml(truncatedUrl)}</code></td>
+            <td>${alertTypes}</td>
+            <td>${severityFilter}</td>
+            <td>${statusBadge}</td>
+            <td>
+                <div class="btn-group btn-group-sm" role="group">
+                    <button class="btn btn-outline-primary" onclick="testWebhook(${webhook.id})" title="Test">
+                        <i class="bi bi-send"></i>
+                    </button>
+                    <a href="/webhooks/${webhook.id}/edit" class="btn btn-outline-primary" title="Edit">
+                        <i class="bi bi-pencil"></i>
+                    </a>
+                    <a href="/webhooks/${webhook.id}/logs" class="btn btn-outline-info" title="Logs">
+                        <i class="bi bi-list-ul"></i>
+                    </a>
+                    <button class="btn btn-outline-danger" onclick="deleteWebhook(${webhook.id}, '${escapeHtml(webhook.name)}')" title="Delete">
+                        <i class="bi bi-trash"></i>
+                    </button>
+                </div>
+            </td>
+        `;
+        tbody.appendChild(row);
+    });
+}
+
+function renderPagination(currentPage, totalPages, totalItems) {
+    const pagination = document.getElementById('pagination');
+    pagination.innerHTML = '';
+
+    if (totalPages <= 1) {
+        document.getElementById('pagination-container').style.display = 'none';
+        return;
+    }
+
+    document.getElementById('pagination-container').style.display = 'block';
+
+    // Previous button
+    const prevLi = document.createElement('li');
+    prevLi.className = `page-item ${currentPage === 1 ? 'disabled' : ''}`;
+    prevLi.innerHTML = `<a class="page-link" href="#" onclick="changePage(${currentPage - 1}); return false;">Previous</a>`;
+    pagination.appendChild(prevLi);
+
+    // Page numbers
+    for (let i = 1; i <= totalPages; i++) {
+        if (i === 1 || i === totalPages || (i >= currentPage - 2 && i <= currentPage + 2)) {
+            const li = document.createElement('li');
+            li.className = `page-item ${i === currentPage ? 'active' : ''}`;
+            li.innerHTML = `<a class="page-link" href="#" onclick="changePage(${i}); return false;">${i}</a>`;
+            pagination.appendChild(li);
+        } else if (i === currentPage - 3 || i === currentPage + 3) {
+            const li = document.createElement('li');
+            li.className = 'page-item disabled';
+            li.innerHTML = '<a class="page-link" href="#">...</a>';
+            pagination.appendChild(li);
+        }
+    }
+
+    // Next button
+    const nextLi = document.createElement('li');
+    nextLi.className = `page-item ${currentPage === totalPages ? 'disabled' : ''}`;
+    nextLi.innerHTML = `<a class="page-link" href="#" onclick="changePage(${currentPage + 1}); return false;">Next</a>`;
+    pagination.appendChild(nextLi);
+}
+
+function changePage(page) {
+    currentPage = page;
+    loadWebhooks(page);
+}
+
+async function testWebhook(id) {
+    if (!confirm('Send a test payload to this webhook?')) return;
+
+    try {
+        const response = await fetch(`/api/webhooks/${id}/test`, { method: 'POST' });
+        const result = await response.json();
+
+        if (result.status === 'success') {
+            alert(`Test successful!\nHTTP ${result.status_code}\n${result.message}`);
+        } else {
+            alert(`Test failed:\n${result.message}`);
+        }
+    } catch (error) {
+        console.error('Error testing webhook:', error);
+        alert('Failed to test webhook');
+    }
+}
+
+async function deleteWebhook(id, name) {
+    if (!confirm(`Are you sure you want to delete webhook "${name}"?`)) return;
+
+    try {
+        const response = await fetch(`/api/webhooks/${id}`, { method: 'DELETE' });
+        const result = await response.json();
+
+        if (result.status === 'success') {
+            alert('Webhook deleted successfully');
+            loadWebhooks(currentPage);
+        } else {
+            alert(`Failed to delete webhook: ${result.message}`);
+        }
+    } catch (error) {
+        console.error('Error deleting webhook:', error);
+        alert('Failed to delete webhook');
+    }
+}
+
+function getSeverityColor(severity) {
+    const colors = {
+        'critical': 'danger',
+        'warning': 'warning',
+        'info': 'info'
+    };
+    return colors[severity] || 'secondary';
+}
+
+function escapeHtml(text) {
+    const div = document.createElement('div');
+    div.textContent = text;
+    return div.innerHTML;
+}
+
+// Load webhooks on page load
+document.addEventListener('DOMContentLoaded', () => {
+    loadWebhooks(1);
+});
+</script>
+{% endblock %}

app/web/templates/webhooks/logs.html

@@ -0,0 +1,328 @@
+{% extends "base.html" %}
+
+{% block title %}Webhook Logs - {{ webhook.name }} - SneakyScanner{% endblock %}
+
+{% block content %}
+<div class="row mt-4">
+    <div class="col-12 mb-4">
+        <h1 style="color: #60a5fa;">Webhook Delivery Logs</h1>
+        <nav aria-label="breadcrumb">
+            <ol class="breadcrumb">
+                <li class="breadcrumb-item"><a href="{{ url_for('webhooks.list_webhooks') }}">Webhooks</a></li>
+                <li class="breadcrumb-item active">{{ webhook.name }}</li>
+            </ol>
+        </nav>
+    </div>
+</div>
+
+<!-- Webhook Info -->
+<div class="row mb-4">
+    <div class="col-12">
+        <div class="card">
+            <div class="card-body">
+                <div class="row">
+                    <div class="col-md-6">
+                        <h5 class="card-title">{{ webhook.name }}</h5>
+                        <p class="text-muted mb-1"><strong>URL:</strong> <code>{{ webhook.url }}</code></p>
+                        <p class="text-muted mb-0">
+                            <strong>Status:</strong>
+                            {% if webhook.enabled %}
+                                <span class="badge bg-success">Enabled</span>
+                            {% else %}
+                                <span class="badge bg-secondary">Disabled</span>
+                            {% endif %}
+                        </p>
+                    </div>
+                    <div class="col-md-6 text-md-end">
+                        <a href="{{ url_for('webhooks.edit_webhook', webhook_id=webhook.id) }}" class="btn btn-primary">
+                            <i class="bi bi-pencil"></i> Edit Webhook
+                        </a>
+                    </div>
+                </div>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Filters -->
+<div class="row mb-4">
+    <div class="col-12">
+        <div class="card">
+            <div class="card-body">
+                <div class="row g-3">
+                    <div class="col-md-4">
+                        <label for="status-filter" class="form-label">Status</label>
+                        <select class="form-select" id="status-filter">
+                            <option value="">All</option>
+                            <option value="success">Success</option>
+                            <option value="failed">Failed</option>
+                        </select>
+                    </div>
+                    <div class="col-md-4 d-flex align-items-end">
+                        <button type="button" class="btn btn-primary w-100" onclick="applyFilter()">
+                            <i class="bi bi-funnel"></i> Apply Filter
+                        </button>
+                    </div>
+                    <div class="col-md-4 d-flex align-items-end">
+                        <button type="button" class="btn btn-outline-secondary w-100" onclick="refreshLogs()">
+                            <i class="bi bi-arrow-clockwise"></i> Refresh
+                        </button>
+                    </div>
+                </div>
+            </div>
+        </div>
+    </div>
+</div>
+
+<!-- Loading indicator -->
+<div id="loading" class="text-center my-5">
+    <div class="spinner-border text-primary" role="status">
+        <span class="visually-hidden">Loading...</span>
+    </div>
+</div>
+
+<!-- Logs table -->
+<div id="logs-container" style="display: none;">
+    <div class="row mb-4">
+        <div class="col-12">
+            <div class="card">
+                <div class="card-body">
+                    <div class="table-responsive">
+                        <table class="table table-hover">
+                            <thead>
+                                <tr>
+                                    <th>Timestamp</th>
+                                    <th>Alert</th>
+                                    <th>Status</th>
+                                    <th>HTTP Code</th>
+                                    <th>Attempt</th>
+                                    <th>Details</th>
+                                </tr>
+                            </thead>
+                            <tbody id="logs-tbody">
+                                <!-- Populated via JavaScript -->
+                            </tbody>
+                        </table>
+                    </div>
+                </div>
+            </div>
+        </div>
+    </div>
+
+    <!-- Pagination -->
+    <nav aria-label="Logs pagination" id="pagination-container">
+        <ul class="pagination justify-content-center" id="pagination">
+            <!-- Populated via JavaScript -->
+        </ul>
+    </nav>
+</div>
+
+<!-- Empty state -->
+<div id="empty-state" class="text-center my-5" style="display: none;">
+    <i class="bi bi-list-ul" style="font-size: 4rem; color: #94a3b8;"></i>
+    <p class="text-muted mt-3">No delivery logs yet.</p>
+    <p class="small text-muted">Logs will appear here after alerts trigger this webhook.</p>
+</div>
+
+<!-- Modal for log details -->
+<div class="modal fade" id="logDetailModal" tabindex="-1" aria-hidden="true">
+    <div class="modal-dialog modal-lg">
+        <div class="modal-content">
+            <div class="modal-header">
+                <h5 class="modal-title">Delivery Log Details</h5>
+                <button type="button" class="btn-close" data-bs-dismiss="modal" aria-label="Close"></button>
+            </div>
+            <div class="modal-body">
+                <div id="modal-content">
+                    <!-- Populated via JavaScript -->
+                </div>
+            </div>
+            <div class="modal-footer">
+                <button type="button" class="btn btn-secondary" data-bs-dismiss="modal">Close</button>
+            </div>
+        </div>
+    </div>
+</div>
+
+{% endblock %}
+
+{% block scripts %}
+<script>
+const webhookId = {{ webhook.id }};
+let currentPage = 1;
+let currentStatus = '';
+const perPage = 20;
+
+async function loadLogs(page = 1, status = '') {
+    try {
+        let url = `/api/webhooks/${webhookId}/logs?page=${page}&per_page=${perPage}`;
+        if (status) {
+            url += `&status=${status}`;
+        }
+
+        const response = await fetch(url);
+        const data = await response.json();
+
+        if (data.logs && data.logs.length > 0) {
+            renderLogs(data.logs);
+            renderPagination(data.page, data.pages, data.total);
+            document.getElementById('logs-container').style.display = 'block';
+            document.getElementById('empty-state').style.display = 'none';
+        } else {
+            document.getElementById('logs-container').style.display = 'none';
+            document.getElementById('empty-state').style.display = 'block';
+        }
+    } catch (error) {
+        console.error('Error loading logs:', error);
+        alert('Failed to load delivery logs');
+    } finally {
+        document.getElementById('loading').style.display = 'none';
+    }
+}
+
+function renderLogs(logs) {
+    const tbody = document.getElementById('logs-tbody');
+    tbody.innerHTML = '';
+
+    logs.forEach(log => {
+        const row = document.createElement('tr');
+
+        // Format timestamp
+        const timestamp = new Date(log.delivered_at).toLocaleString();
+
+        // Status badge
+        const statusBadge = log.status === 'success' ?
+            '<span class="badge bg-success">Success</span>' :
+            '<span class="badge bg-danger">Failed</span>';
+
+        // HTTP code badge
+        const httpBadge = log.response_code ?
+            `<span class="badge ${log.response_code < 400 ? 'bg-success' : 'bg-danger'}">${log.response_code}</span>` :
+            '<span class="text-muted">N/A</span>';
+
+        // Alert info
+        const alertInfo = log.alert_type ?
+            `<span class="badge bg-secondary">${log.alert_type}</span><br><small class="text-muted">${escapeHtml(log.alert_message || '')}</small>` :
+            `<small class="text-muted">Alert #${log.alert_id}</small>`;
+
+        row.innerHTML = `
+            <td><small>${timestamp}</small></td>
+            <td>${alertInfo}</td>
+            <td>${statusBadge}</td>
+            <td>${httpBadge}</td>
+            <td>${log.attempt_number || 1}</td>
+            <td>
+                <button class="btn btn-sm btn-outline-primary" onclick="showLogDetails(${JSON.stringify(log).replace(/"/g, '&quot;')})">
+                    <i class="bi bi-eye"></i> View
+                </button>
+            </td>
+        `;
+        tbody.appendChild(row);
+    });
+}
+
+function renderPagination(currentPage, totalPages, totalItems) {
+    const pagination = document.getElementById('pagination');
+    pagination.innerHTML = '';
+
+    if (totalPages <= 1) {
+        document.getElementById('pagination-container').style.display = 'none';
+        return;
+    }
+
+    document.getElementById('pagination-container').style.display = 'block';
+
+    // Previous button
+    const prevLi = document.createElement('li');
+    prevLi.className = `page-item ${currentPage === 1 ? 'disabled' : ''}`;
+    prevLi.innerHTML = `<a class="page-link" href="#" onclick="changePage(${currentPage - 1}); return false;">Previous</a>`;
+    pagination.appendChild(prevLi);
+
+    // Page numbers
+    for (let i = 1; i <= totalPages; i++) {
+        if (i === 1 || i === totalPages || (i >= currentPage - 2 && i <= currentPage + 2)) {
+            const li = document.createElement('li');
+            li.className = `page-item ${i === currentPage ? 'active' : ''}`;
+            li.innerHTML = `<a class="page-link" href="#" onclick="changePage(${i}); return false;">${i}</a>`;
+            pagination.appendChild(li);
+        } else if (i === currentPage - 3 || i === currentPage + 3) {
+            const li = document.createElement('li');
+            li.className = 'page-item disabled';
+            li.innerHTML = '<a class="page-link" href="#">...</a>';
+            pagination.appendChild(li);
+        }
+    }
+
+    // Next button
+    const nextLi = document.createElement('li');
+    nextLi.className = `page-item ${currentPage === totalPages ? 'disabled' : ''}`;
+    nextLi.innerHTML = `<a class="page-link" href="#" onclick="changePage(${currentPage + 1}); return false;">Next</a>`;
+    pagination.appendChild(nextLi);
+}
+
+function changePage(page) {
+    currentPage = page;
+    loadLogs(page, currentStatus);
+}
+
+function applyFilter() {
+    currentStatus = document.getElementById('status-filter').value;
+    currentPage = 1;
+    loadLogs(1, currentStatus);
+}
+
+function refreshLogs() {
+    loadLogs(currentPage, currentStatus);
+}
+
+function showLogDetails(log) {
+    const modalContent = document.getElementById('modal-content');
+
+    let detailsHTML = `
+        <div class="mb-3">
+            <strong>Log ID:</strong> ${log.id}<br>
+            <strong>Alert ID:</strong> ${log.alert_id}<br>
+            <strong>Status:</strong> <span class="badge ${log.status === 'success' ? 'bg-success' : 'bg-danger'}">${log.status}</span><br>
+            <strong>HTTP Code:</strong> ${log.response_code || 'N/A'}<br>
+            <strong>Attempt:</strong> ${log.attempt_number || 1}<br>
+            <strong>Delivered At:</strong> ${new Date(log.delivered_at).toLocaleString()}
+        </div>
+    `;
+
+    if (log.response_body) {
+        detailsHTML += `
+            <div class="mb-3">
+                <strong>Response Body:</strong>
+                <pre class="bg-dark text-light p-2 rounded mt-2"><code>${escapeHtml(log.response_body)}</code></pre>
+            </div>
+        `;
+    }
+
+    if (log.error_message) {
+        detailsHTML += `
+            <div class="mb-3">
+                <strong>Error Message:</strong>
+                <div class="alert alert-danger mt-2">${escapeHtml(log.error_message)}</div>
+            </div>
+        `;
+    }
+
+    modalContent.innerHTML = detailsHTML;
+
+    const modal = new bootstrap.Modal(document.getElementById('logDetailModal'));
+    modal.show();
+}
+
+function escapeHtml(text) {
+    if (!text) return '';
+    const div = document.createElement('div');
+    div.textContent = text;
+    return div.innerHTML;
+}
+
+// Load logs on page load
+document.addEventListener('DOMContentLoaded', () => {
+    loadLogs(1);
+});
+</script>
+{% endblock %}

app/web/utils/pagination.py

@@ -53,6 +53,46 @@ class PaginatedResult:
         """Get next page number."""
         return self.page + 1 if self.has_next else None
 
+    @property
+    def prev_num(self) -> int:
+        """Alias for prev_page (Flask-SQLAlchemy compatibility)."""
+        return self.prev_page
+
+    @property
+    def next_num(self) -> int:
+        """Alias for next_num (Flask-SQLAlchemy compatibility)."""
+        return self.next_page
+
+    def iter_pages(self, left_edge=1, left_current=1, right_current=2, right_edge=1):
+        """
+        Generate page numbers for pagination display.
+
+        Yields page numbers and None for gaps, compatible with Flask-SQLAlchemy's
+        pagination.iter_pages() method.
+
+        Args:
+            left_edge: Number of pages to show on the left edge
+            left_current: Number of pages to show left of current page
+            right_current: Number of pages to show right of current page
+            right_edge: Number of pages to show on the right edge
+
+        Yields:
+            int or None: Page number or None for gaps
+
+        Example:
+            For 100 pages, current page 50:
+            Yields: 1, None, 48, 49, 50, 51, 52, None, 100
+        """
+        last = 0
+        for num in range(1, self.pages + 1):
+            if num <= left_edge or \
+               (num > self.page - left_current - 1 and num < self.page + right_current) or \
+               num > self.pages - right_edge:
+                if last + 1 != num:
+                    yield None
+                yield num
+                last = num
+
     def to_dict(self) -> Dict[str, Any]:
         """
         Convert to dictionary for API responses.

app/web/utils/settings.py

@@ -7,8 +7,8 @@ for sensitive values like passwords and API tokens.
 
 import json
 import os
-from datetime import datetime
-from typing import Any, Dict, List, Optional
+from datetime import datetime, timezone
+from typing import Any, Dict, Optional
 
 import bcrypt
 from cryptography.fernet import Fernet
@@ -32,6 +32,11 @@ class SettingsManager:
         'encryption_key',
     }
 
+    # Keys that are read-only (managed by developer, not user-editable)
+    READ_ONLY_KEYS = {
+        'encryption_key',
+    }
+
     def __init__(self, db_session: Session, encryption_key: Optional[bytes] = None):
         """
         Initialize the settings manager.
@@ -69,11 +74,11 @@ class SettingsManager:
         return new_key
 
     def _store_raw(self, key: str, value: str) -> None:
-        """Store a setting without encryption (internal use only)."""
+        """Store a setting without encryption (internal use only). Bypasses read-only check."""
         setting = self.db.query(Setting).filter_by(key=key).first()
         if setting:
             setting.value = value
-            setting.updated_at = datetime.utcnow()
+            setting.updated_at = datetime.now(timezone.utc)
         else:
             setting = Setting(key=key, value=value)
             self.db.add(setting)
@@ -128,7 +133,11 @@ class SettingsManager:
 
         return value
 
-    def set(self, key: str, value: Any, encrypt: bool = None) -> None:
+    def _is_read_only(self, key: str) -> bool:
+        """Check if a setting key is read-only."""
+        return key in self.READ_ONLY_KEYS
+
+    def set(self, key: str, value: Any, encrypt: bool = None, allow_read_only: bool = False) -> None:
         """
         Set a setting value.
 
@@ -136,7 +145,15 @@ class SettingsManager:
             key: Setting key
             value: Setting value (will be JSON-encoded if dict/list)
             encrypt: Force encryption on/off (None = auto-detect from ENCRYPTED_KEYS)
+            allow_read_only: If True, allows setting read-only keys (internal use only)
+
+        Raises:
+            ValueError: If attempting to set a read-only key without allow_read_only=True
         """
+        # Prevent modification of read-only keys unless explicitly allowed
+        if not allow_read_only and self._is_read_only(key):
+            raise ValueError(f"Setting '{key}' is read-only and cannot be modified via API")
+
         # Convert complex types to JSON
         if isinstance(value, (dict, list)):
             value_str = json.dumps(value)
@@ -153,7 +170,7 @@ class SettingsManager:
         setting = self.db.query(Setting).filter_by(key=key).first()
         if setting:
             setting.value = value_str
-            setting.updated_at = datetime.utcnow()
+            setting.updated_at = datetime.now(timezone.utc)
         else:
             setting = Setting(key=key, value=value_str)
             self.db.add(setting)
@@ -251,7 +268,8 @@ class SettingsManager:
         for key, value in defaults.items():
             # Only set if doesn't exist
             if self.db.query(Setting).filter_by(key=key).first() is None:
-                self.set(key, value)
+                # Use allow_read_only=True for initializing defaults
+                self.set(key, value, allow_read_only=True)
 
 
 class PasswordManager:

docker-compose.yml

@@ -5,9 +5,9 @@ services:
     build: .
     image: sneakyscanner:latest
     container_name: sneakyscanner-web
-    # Override entrypoint to run Flask app instead of scanner
-    entrypoint: ["python3", "-u"]
-    command: ["-m", "web.app"]
+    # Use entrypoint script that auto-initializes database on first run
+    entrypoint: ["/docker-entrypoint.sh"]
+    command: ["python3", "-u", "-m", "web.app"]
     # Note: Using host network mode for scanner capabilities, so no port mapping needed
     # The Flask app will be accessible at http://localhost:5000
     volumes:
@@ -28,7 +28,10 @@ services:
       - FLASK_PORT=5000
       # Database configuration (SQLite in mounted volume for persistence)
       - DATABASE_URL=sqlite:////app/data/sneakyscanner.db
+      # Initial password for first run (leave empty to auto-generate)
+      - INITIAL_PASSWORD=${INITIAL_PASSWORD:-}
       # Security settings
+      # IMPORTANT: Set these in .env file or the application will fail to start!
       - SECRET_KEY=${SECRET_KEY:-dev-secret-key-change-in-production}
       - SNEAKYSCANNER_ENCRYPTION_KEY=${SNEAKYSCANNER_ENCRYPTION_KEY:-}
       # Optional: CORS origins (comma-separated)

docs/DEPLOYMENT.md

@@ -74,6 +74,31 @@ docker compose version
 
 For users who want to get started immediately with the web application:
 
+**Option 1: Automated Setup (Recommended)**
+
+```bash
+# 1. Clone the repository
+git clone <repository-url>
+cd SneakyScan
+
+# 2. Run the setup script
+./setup.sh
+
+# 3. Access the web interface
+# Open browser to: http://localhost:5000
+# Login with password from ./admin_password.txt or ./logs/admin_password.txt
+```
+
+The setup script automatically:
+- Generates secure random keys (SECRET_KEY, ENCRYPTION_KEY)
+- Prompts for password or generates a random one
+- Creates required directories
+- Builds Docker image
+- Starts the application
+- Auto-initializes database on first run
+
+**Option 2: Manual Setup**
+
 ```bash
 # 1. Clone the repository
 git clone <repository-url>
@@ -82,18 +107,17 @@ cd SneakyScan
 # 2. Create environment file
 cp .env.example .env
 # Edit .env and set SECRET_KEY and SNEAKYSCANNER_ENCRYPTION_KEY
+# Optionally set INITIAL_PASSWORD (leave blank for auto-generation)
 nano .env
 
-# 3. Build the Docker image
-docker compose build
+# 3. Build and start (database auto-initializes on first run)
+docker compose up --build -d
 
-# 4. Initialize the database and set password
-docker compose run --rm init-db --password "YourSecurePassword"
+# 4. Check logs for auto-generated password (if not set in .env)
+docker compose logs web | grep "Password"
+# Or check: ./logs/admin_password.txt
 
-# 5. Start the application
-docker compose up -d
-
-# 6. Access the web interface
+# 5. Access the web interface
 # Open browser to: http://localhost:5000
 ```
 
@@ -126,7 +150,10 @@ SneakyScanner is configured via environment variables. The recommended approach
 cp .env.example .env
 
 # Generate secure keys
+# SECRET_KEY: Flask session secret (64-character hex string)
 python3 -c "import secrets; print('SECRET_KEY=' + secrets.token_hex(32))" >> .env
+
+# SNEAKYSCANNER_ENCRYPTION_KEY: Fernet key for database encryption (32 url-safe base64 bytes)
 python3 -c "from cryptography.fernet import Fernet; print('SNEAKYSCANNER_ENCRYPTION_KEY=' + Fernet.generate_key().decode())" >> .env
 
 # Edit other settings as needed
@@ -142,6 +169,7 @@ nano .env
 | `SECRET_KEY` | Flask session secret (change in production!) | `dev-secret-key-change-in-production` | **Yes** |
 | `SNEAKYSCANNER_ENCRYPTION_KEY` | Encryption key for sensitive settings | (empty) | **Yes** |
 | `DATABASE_URL` | SQLite database path | `sqlite:////app/data/sneakyscanner.db` | Yes |
+| `INITIAL_PASSWORD` | Password for first-run initialization (leave empty to auto-generate) | (empty) | No |
 | `LOG_LEVEL` | Logging level (DEBUG, INFO, WARNING, ERROR) | `INFO` | No |
 | `SCHEDULER_EXECUTORS` | Number of concurrent scan threads | `2` | No |
 | `SCHEDULER_JOB_DEFAULTS_MAX_INSTANCES` | Max instances of same job | `3` | No |
@@ -223,28 +251,56 @@ docker images | grep sneakyscanner
 
 ### Step 4: Initialize Database
 
-The database must be initialized before first use. The init-db service uses a profile, so you need to explicitly run it:
+**Automatic Initialization (Recommended)**
+
+As of Phase 5, the database is automatically initialized on first run:
+
+```bash
+# Just start the application
+docker compose up -d
+
+# On first run, the entrypoint script will:
+# - Detect no existing database
+# - Generate a random password (if INITIAL_PASSWORD not set in .env)
+# - Save password to ./logs/admin_password.txt
+# - Initialize database schema
+# - Create default settings and alert rules
+# - Start the Flask application
+
+# Check logs to see the auto-generated password
+docker compose logs web | grep "Password"
+
+# Or view the password file
+cat logs/admin_password.txt
+```
+
+**Manual Initialization (Advanced)**
+
+You can still manually initialize the database if needed:
 
 ```bash
 # Initialize database and set application password
-docker compose -f docker-compose.yml run --rm init-db --password "YourSecurePassword"
+docker compose run --rm init-db --password "YourSecurePassword" --force
 
 # The init-db command will:
 # - Create database schema
-# - Run all Alembic migrations
 # - Set the application password (bcrypt hashed)
 # - Create default settings with encryption
+# - Create default alert rules
 
 # Verify database was created
 ls -lh data/sneakyscanner.db
 ```
 
-**Password Requirements:**
+**Password Management:**
+- Leave `INITIAL_PASSWORD` blank in `.env` for auto-generation
+- Auto-generated passwords are saved to `./logs/admin_password.txt`
+- For custom password, set `INITIAL_PASSWORD` in `.env`
 - Minimum 8 characters recommended
 - Use a strong, unique password
 - Store securely (password manager)
 
-**Note**: The init-db service is defined with `profiles: [tools]` in docker-compose.yml, which means it won't start automatically with `docker compose up`.
+**Note**: The init-db service is defined with `profiles: [tools]` in docker-compose.yml, which means it won't start automatically with `docker compose up`. However, the web service now handles initialization automatically via the entrypoint script.
 
 ### Step 5: Verify Configuration
 
@@ -699,17 +755,25 @@ tail -f logs/sneakyscanner.log
 
 ```bash
 # Check logs for errors
-docker compose -f docker-compose.yml logs web
+docker compose logs web
 
 # Common issues:
-# 1. Database not initialized - run init-db first
-# 2. Permission issues with volumes - check directory ownership
-# 3. Port 5000 already in use - change FLASK_PORT or stop conflicting service
+# 1. Permission issues with volumes - check directory ownership
+# 2. Port 5000 already in use - change FLASK_PORT or stop conflicting service
+# 3. Database initialization failed - check logs for specific error
+
+# Check if database initialization is stuck
+docker compose logs web | grep -A 20 "First Run Detected"
+
+# If initialization failed, clean up and retry
+docker compose down
+rm -rf data/.db_initialized  # Remove marker file
+docker compose up -d
 ```
 
 ### Database Initialization Fails
 
-**Problem**: `init_db.py` fails with errors
+**Problem**: Automatic database initialization fails on first run
 
 ```bash
 # Check database directory permissions
@@ -718,12 +782,37 @@ ls -la data/
 # Fix permissions if needed
 sudo chown -R $USER:$USER data/
 
-# Verify SQLite is accessible
-sqlite3 data/sneakyscanner.db "SELECT 1;" 2>&1
+# View initialization logs
+docker compose logs web | grep -A 50 "Initializing database"
 
-# Remove corrupted database and reinitialize
-rm data/sneakyscanner.db
-docker compose -f docker-compose.yml run --rm init-db --password "YourPassword"
+# Clean up and retry initialization
+docker compose down
+rm -rf data/sneakyscanner.db data/.db_initialized
+docker compose up -d
+
+# Or manually initialize with specific password
+docker compose down
+rm -rf data/sneakyscanner.db data/.db_initialized
+docker compose run --rm init-db --password "YourPassword" --force
+docker compose up -d
+```
+
+**Can't Find Password File**
+
+**Problem**: Password file not created or can't be found
+
+```bash
+# Check both possible locations
+cat admin_password.txt      # Created by setup.sh
+cat logs/admin_password.txt  # Created by Docker entrypoint
+
+# Check container logs for password
+docker compose logs web | grep -i password
+
+# If password file is missing, manually set one
+docker compose down
+docker compose run --rm init-db --password "YourNewPassword" --force
+docker compose up -d
 ```
 
 ### Scans Fail with "Permission Denied"

setup.sh

@@ -0,0 +1,150 @@
+#!/bin/bash
+set -e
+
+# SneakyScanner First-Run Setup Script
+# This script helps you get started quickly with SneakyScanner
+
+echo "================================================"
+echo "  SneakyScanner - First Run Setup"
+echo "================================================"
+echo ""
+
+# Function to generate random key for Flask SECRET_KEY
+generate_secret_key() {
+    openssl rand -hex 32 2>/dev/null || python3 -c "import secrets; print(secrets.token_hex(32))"
+}
+
+# Function to generate Fernet encryption key (32 url-safe base64-encoded bytes)
+generate_fernet_key() {
+    python3 -c "from cryptography.fernet import Fernet; print(Fernet.generate_key().decode())" 2>/dev/null || \
+    openssl rand -base64 32 | head -c 44
+}
+
+# Check if .env exists
+if [ -f .env ]; then
+    echo "✓ .env file already exists"
+    read -p "Do you want to regenerate it? (y/N): " REGENERATE
+    if [ "$REGENERATE" != "y" ] && [ "$REGENERATE" != "Y" ]; then
+        echo "Skipping .env creation..."
+        SKIP_ENV=true
+    fi
+fi
+
+# Create or update .env
+if [ "$SKIP_ENV" != "true" ]; then
+    echo ""
+    echo "Creating .env file..."
+
+    # Generate secure keys
+    SECRET_KEY=$(generate_secret_key)
+    ENCRYPTION_KEY=$(generate_fernet_key)
+
+    # Ask for initial password
+    echo ""
+    echo "Set an initial password for the web interface:"
+    read -s -p "Password (or press Enter to generate random password): " INITIAL_PASSWORD
+    echo ""
+
+    if [ -z "$INITIAL_PASSWORD" ]; then
+        echo "Generating random password..."
+        # Generate a 32-character alphanumeric password
+        INITIAL_PASSWORD=$(cat /dev/urandom | tr -dc 'A-Za-z0-9' | head -c 32)
+        # Save password to file in project root (avoid permission issues with mounted volumes)
+        echo "$INITIAL_PASSWORD" > admin_password.txt
+        echo "✓ Random password generated and saved to: ./admin_password.txt"
+        PASSWORD_SAVED=true
+    fi
+
+    # Create .env file
+    cat > .env << EOF
+# Flask Configuration
+FLASK_ENV=production
+FLASK_DEBUG=false
+
+# Security Keys (randomly generated)
+SECRET_KEY=$SECRET_KEY
+SNEAKYSCANNER_ENCRYPTION_KEY=$ENCRYPTION_KEY
+
+# Initial Password
+INITIAL_PASSWORD=$INITIAL_PASSWORD
+
+# Database Configuration
+DATABASE_URL=sqlite:////app/data/sneakyscanner.db
+
+# Optional: Logging
+LOG_LEVEL=INFO
+
+# Optional: CORS (comma-separated origins, or * for all)
+CORS_ORIGINS=*
+EOF
+
+    echo "✓ .env file created with secure keys"
+fi
+
+# Create required directories
+echo ""
+echo "Creating required directories..."
+mkdir -p data logs output configs
+echo "✓ Directories created"
+
+# Check if Docker is running
+echo ""
+echo "Checking Docker..."
+if ! docker info > /dev/null 2>&1; then
+    echo "✗ Docker is not running or not installed"
+    echo "Please install Docker and start the Docker daemon"
+    exit 1
+fi
+echo "✓ Docker is running"
+
+# Build and start
+echo ""
+echo "Building and starting SneakyScanner..."
+echo "This may take a few minutes on first run..."
+echo ""
+
+docker compose build
+
+echo ""
+echo "Starting SneakyScanner..."
+docker compose up -d
+
+# Wait for service to be healthy
+echo ""
+echo "Waiting for application to start..."
+sleep 5
+
+# Check if container is running
+if docker ps | grep -q sneakyscanner-web; then
+    echo ""
+    echo "================================================"
+    echo "  ✓ SneakyScanner is Running!"
+    echo "================================================"
+    echo ""
+    echo "Web Interface: http://localhost:5000"
+    echo ""
+    echo "Login with:"
+    if [ -z "$SKIP_ENV" ]; then
+        if [ "$PASSWORD_SAVED" = "true" ]; then
+            echo "  Password saved in: ./admin_password.txt"
+            echo "  Password: $INITIAL_PASSWORD"
+        else
+            echo "  Password: $INITIAL_PASSWORD"
+        fi
+    else
+        echo "  Password: (check your .env file or ./admin_password.txt)"
+    fi
+    echo ""
+    echo "Useful commands:"
+    echo "  docker compose logs -f     # View logs"
+    echo "  docker compose stop        # Stop the service"
+    echo "  docker compose restart     # Restart the service"
+    echo ""
+    echo "⚠  IMPORTANT: Change your password after first login!"
+    echo "================================================"
+else
+    echo ""
+    echo "✗ Container failed to start. Check logs with:"
+    echo "  docker compose logs"
+    exit 1
+fi