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+# Deployment Checklist: Secure Database Implementation
+
+Use this checklist when deploying the secure database implementation to production.
+
+## Pre-Deployment
+
+### 1. Environment Preparation
+- [ ] Generate encryption key: `openssl rand -hex 32`
+- [ ] Generate JWT secret: `openssl rand -hex 32`
+- [ ] Save keys securely (password manager, secrets vault, etc.)
+- [ ] Add keys to environment configuration (docker-compose.yml or .env)
+- [ ] Verify keys are 64 characters (hex format)
+
+### 2. Backup Current System
+- [ ] Backup current JSON files (users.json, user-sessions.json, affiliates.json)
+- [ ] Document current user count
+- [ ] Document current session count
+- [ ] Create rollback plan
+- [ ] Test backup restoration procedure
+
+### 3. Testing in Staging
+- [ ] Deploy to staging environment
+- [ ] Verify database initialization
+- [ ] Test user creation
+- [ ] Test session management
+- [ ] Test encryption/decryption
+- [ ] Test migration (if applicable)
+- [ ] Verify audit logging
+- [ ] Test rollback to JSON mode
+
+## Deployment
+
+### Option A: New Deployment (No Existing Data)
+
+```bash
+# 1. Set environment variables
+export DATABASE_ENCRYPTION_KEY=<your-64-char-hex-key>
+export JWT_SECRET=<your-64-char-hex-key>
+
+# 2. Deploy container
+docker-compose up -d
+
+# 3. Verify logs
+docker logs shopify-ai-builder | grep "Database setup complete"
+
+# Expected output:
+# ✅ Database setup complete!
+```
+
+**Checklist:**
+- [ ] Database created at `.data/shopify_ai.db`
+- [ ] Encryption keys saved to `.data/.encryption_key` and `.data/.jwt_secret`
+- [ ] All 10 tables created
+- [ ] No errors in logs
+
+### Option B: Migration from JSON Files
+
+```bash
+# 1. Keep JSON mode active initially
+export USE_JSON_DATABASE=1
+export DATABASE_ENCRYPTION_KEY=<your-64-char-hex-key>
+export JWT_SECRET=<your-64-char-hex-key>
+
+# 2. Deploy container
+docker-compose up -d
+
+# 3. Verify JSON mode is active
+docker logs shopify-ai-builder | grep "JSON"
+# Expected: "Running in JSON compatibility mode"
+
+# 4. Run migration inside container
+docker exec shopify-ai-builder node /opt/webchat/scripts/migrate-to-database.js
+
+# 5. Verify migration results
+docker exec shopify-ai-builder sqlite3 /home/web/data/.data/shopify_ai.db "SELECT COUNT(*) FROM users;"
+docker exec shopify-ai-builder sqlite3 /home/web/data/.data/shopify_ai.db "SELECT COUNT(*) FROM sessions;"
+
+# 6. Switch to database mode
+export USE_JSON_DATABASE=0
+docker-compose restart shopify-ai-builder
+
+# 7. Verify database mode
+docker logs shopify-ai-builder | grep -v "JSON"
+```
+
+**Checklist:**
+- [ ] Migration backup created in `.data/migration_backup_*`
+- [ ] All users migrated (verify count matches)
+- [ ] All sessions migrated (verify count matches)
+- [ ] All affiliates migrated (verify count matches)
+- [ ] Database mode active (no "JSON" in logs)
+- [ ] Application functioning normally
+
+## Post-Deployment
+
+### 1. Verification
+- [ ] Database file exists and is accessible
+- [ ] Encryption keys persisted
+- [ ] Users can log in
+- [ ] Sessions are created
+- [ ] Audit log is recording events
+- [ ] No errors in application logs
+
+### 2. Smoke Tests
+```bash
+# Test database access
+docker exec shopify-ai-builder sqlite3 /home/web/data/.data/shopify_ai.db ".tables"
+
+# Count records
+docker exec shopify-ai-builder sqlite3 /home/web/data/.data/shopify_ai.db "SELECT COUNT(*) FROM users;"
+docker exec shopify-ai-builder sqlite3 /home/web/data/.data/shopify_ai.db "SELECT COUNT(*) FROM sessions;"
+docker exec shopify-ai-builder sqlite3 /home/web/data/.data/shopify_ai.db "SELECT COUNT(*) FROM audit_log;"
+
+# Check encryption keys
+docker exec shopify-ai-builder test -f /home/web/data/.data/.encryption_key && echo "Encryption key exists"
+docker exec shopify-ai-builder test -f /home/web/data/.data/.jwt_secret && echo "JWT secret exists"
+```
+
+**Checklist:**
+- [ ] All tables exist
+- [ ] Record counts match expectations
+- [ ] Encryption keys exist
+- [ ] Database size is reasonable
+
+### 3. Functional Tests
+- [ ] Create a new user
+- [ ] Log in with user
+- [ ] Verify session created in database
+- [ ] Log out
+- [ ] Verify session removed/expired
+- [ ] Check audit log entries
+
+### 4. Security Verification
+```bash
+# Check file permissions
+docker exec shopify-ai-builder ls -l /home/web/data/.data/
+
+# Verify database is encrypted (should see binary data)
+docker exec shopify-ai-builder head -c 100 /home/web/data/.data/shopify_ai.db | od -c
+
+# Check audit log
+docker exec shopify-ai-builder sqlite3 /home/web/data/.data/shopify_ai.db \
+  "SELECT event_type, COUNT(*) FROM audit_log GROUP BY event_type;"
+```
+
+**Checklist:**
+- [ ] Database file permissions are restrictive
+- [ ] Encryption key file permissions are 600
+- [ ] Database file is binary (not plain text)
+- [ ] Audit log is capturing events
+
+### 5. Performance Check
+- [ ] Application response time normal
+- [ ] Database query time < 1ms for typical operations
+- [ ] WAL mode active: `PRAGMA journal_mode;` returns `wal`
+- [ ] No database locks or conflicts
+- [ ] Memory usage stable
+
+### 6. Monitoring Setup
+- [ ] Database size monitoring enabled
+- [ ] Error log monitoring enabled
+- [ ] Audit log review scheduled
+- [ ] Backup schedule configured
+- [ ] Alert thresholds set
+
+## Rollback Procedure
+
+If issues occur, follow this rollback procedure:
+
+```bash
+# 1. Stop the container
+docker stop shopify-ai-builder
+
+# 2. Set JSON mode
+export USE_JSON_DATABASE=1
+
+# 3. Verify JSON files exist
+docker exec shopify-ai-builder ls -l /home/web/data/.data/*.json
+
+# 4. If JSON files missing, restore from backup
+docker cp backup/users.json shopify-ai-builder:/home/web/data/.data/
+docker cp backup/user-sessions.json shopify-ai-builder:/home/web/data/.data/
+docker cp backup/affiliates.json shopify-ai-builder:/home/web/data/.data/
+
+# 5. Restart in JSON mode
+docker-compose up -d
+
+# 6. Verify JSON mode active
+docker logs shopify-ai-builder | grep "JSON compatibility mode"
+```
+
+**Rollback Checklist:**
+- [ ] JSON mode activated
+- [ ] JSON files present
+- [ ] Application functioning
+- [ ] Users can log in
+- [ ] No data loss confirmed
+
+## Post-Rollback
+
+If rollback was necessary:
+
+- [ ] Document the issue encountered
+- [ ] Review logs for error messages
+- [ ] Test in staging environment again
+- [ ] Fix identified issues
+- [ ] Plan next deployment attempt
+
+## Maintenance
+
+### Daily
+- [ ] Check application logs for errors
+- [ ] Verify database is accessible
+- [ ] Check disk space
+
+### Weekly
+- [ ] Review audit logs
+- [ ] Check database size growth
+- [ ] Verify backups are running
+- [ ] Review performance metrics
+
+### Monthly
+- [ ] Rotate audit logs if needed
+- [ ] Clean up expired sessions
+- [ ] Clean up expired blacklist entries
+- [ ] Review security events
+
+### Quarterly
+- [ ] Update dependencies
+- [ ] Security audit
+- [ ] Performance review
+- [ ] Disaster recovery test
+
+## Troubleshooting
+
+### Database Not Found
+```bash
+# Check if database file exists
+docker exec shopify-ai-builder ls -l /home/web/data/.data/
+
+# Re-run initialization
+docker exec shopify-ai-builder node /opt/webchat/scripts/init-database.js
+```
+
+### Encryption Error
+```bash
+# Verify key exists and is correct length
+docker exec shopify-ai-builder cat /home/web/data/.data/.encryption_key | wc -c
+# Should output 65 (64 chars + newline)
+
+# Check environment variable
+docker exec shopify-ai-builder printenv DATABASE_ENCRYPTION_KEY
+```
+
+### Migration Failed
+```bash
+# Check backup directory
+docker exec shopify-ai-builder ls -l /home/web/data/.data/migration_backup_*/
+
+# Restore from backup if needed
+docker exec shopify-ai-builder cp -r /home/web/data/.data/migration_backup_*/* /home/web/data/.data/
+```
+
+### Performance Issues
+```bash
+# Check WAL mode
+docker exec shopify-ai-builder sqlite3 /home/web/data/.data/shopify_ai.db "PRAGMA journal_mode;"
+
+# Check database size
+docker exec shopify-ai-builder du -h /home/web/data/.data/shopify_ai.db
+
+# Vacuum database if needed (offline)
+docker stop shopify-ai-builder
+docker exec shopify-ai-builder sqlite3 /home/web/data/.data/shopify_ai.db "VACUUM;"
+docker start shopify-ai-builder
+```
+
+## Support Contacts
+
+- **Development Team**: [contact info]
+- **DevOps Team**: [contact info]
+- **Security Team**: [contact info]
+- **On-Call**: [contact info]
+
+## Documentation References
+
+- Implementation Guide: `chat/DATABASE_IMPLEMENTATION.md`
+- Testing Guide: `chat/TESTING_GUIDE.md`
+- Implementation Summary: `IMPLEMENTATION_COMPLETE_SUMMARY.md`
+- Security Plan: `.opencode/plans/IMPLEMENTATION_PLAN_1.2_1.3.md`
+
+---
+
+**Last Updated**: 2026-02-09
+**Version**: 1.0
+**Status**: Production Ready ✅