diff --git a/docker/cron/Dockerfile b/docker/cron/Dockerfile
new file mode 100644
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--- /dev/null
+++ b/docker/cron/Dockerfile
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+FROM ghcr.io/syscoin/syshub-api:master
+
+# Install cron and docker CLI
+USER root
+RUN apt-get update && \
+    apt-get install -y cron docker.io && \
+    apt-get clean && \
+    rm -rf /var/lib/apt/lists/*
+
+# Create log directory
+RUN mkdir -p /var/log && \
+    chmod 755 /var/log
+
+# Copy cron configuration
+COPY docker/cron/crontab /etc/cron.d/key-rotation
+COPY docker/cron/rotate-key-cron.sh /app/docker/cron/rotate-key-cron.sh
+
+# Set permissions
+RUN chmod 0644 /etc/cron.d/key-rotation && \
+    chmod +x /app/docker/cron/rotate-key-cron.sh && \
+    crontab /etc/cron.d/key-rotation
+
+# Create cron log file
+RUN touch /var/log/cron.log
+
+# Start cron in foreground
+CMD ["cron", "-f"]
diff --git a/docker/cron/README.md b/docker/cron/README.md
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+++ b/docker/cron/README.md
@@ -0,0 +1,330 @@
+# Automatic Encryption Key Rotation Setup
+
+This setup provides automated monthly encryption key rotation for 2FA secrets using a cron sidecar container.
+
+## 🏗️ Architecture
+
+```
+┌─────────────────────────────────────────────────────────┐
+│  Docker Compose Stack                                    │
+│                                                          │
+│  ┌──────────────┐          ┌─────────────────────────┐ │
+│  │   api        │◄─────────│  key-rotation-cron      │ │
+│  │  (Node.js)   │  restart │  (Node.js + cron)       │ │
+│  │              │          │                         │ │
+│  │  - Serves    │          │  - Runs monthly         │ │
+│  │    API       │          │  - Rotates key          │ │
+│  │  - Uses      │          │  - Updates .env.api     │ │
+│  │    .env.api  │          │  - Restarts API         │ │
+│  └──────────────┘          └─────────────────────────┘ │
+│         │                            │                  │
+│         └────────────┬───────────────┘                  │
+│                      │                                  │
+│              ┌───────▼────────┐                        │
+│              │  .env.api      │                        │
+│              │  (shared)      │                        │
+│              └────────────────┘                        │
+└─────────────────────────────────────────────────────────┘
+```
+
+## 📋 Files Created
+
+```
+docker/
+└── cron/
+    ├── Dockerfile              # Cron container image
+    ├── crontab                 # Cron schedule (monthly)
+    ├── rotate-key-cron.sh      # Rotation script wrapper
+    ├── docker-compose.cron.yml # Service definition
+    └── README.md               # This file
+```
+
+## 🚀 Setup Instructions
+
+### Step 1: Create Log Directory
+
+```bash
+# On your Hetzner staging server
+cd /path/to/syshub-api
+mkdir -p logs/key-rotation
+chmod 755 logs/key-rotation
+```
+
+### Step 2: Update docker-compose.yml
+
+Add the `key-rotation-cron` service to your existing `docker-compose.yml`:
+
+```yaml
+services:
+  api:
+    # ... existing api service ...
+
+  # Add this new service:
+  key-rotation-cron:
+    build:
+      context: .
+      dockerfile: docker/cron/Dockerfile
+    container_name: syshub-key-rotation-cron
+    restart: unless-stopped
+    env_file:
+      - .env.api
+    volumes:
+      - .env.api:/app/.env:rw
+      - .firebase-service-account.json:/app/.firebase-service-account.json:ro
+      - /var/run/docker.sock:/var/run/docker.sock:ro
+      - ./logs/key-rotation:/var/log:rw
+    network_mode: bridge
+    extra_hosts:
+      - "host.docker.internal:host-gateway"
+    depends_on:
+      - api
+```
+
+### Step 3: Build and Start Cron Container
+
+```bash
+# Build the cron image
+docker-compose build key-rotation-cron
+
+# Start the cron sidecar
+docker-compose up -d key-rotation-cron
+
+# Verify it's running
+docker-compose ps key-rotation-cron
+```
+
+### Step 4: Verify Cron Schedule
+
+```bash
+# Check that cron is configured correctly
+docker exec syshub-key-rotation-cron crontab -l
+
+# Expected output:
+# 0 2 1 * * /app/docker/cron/rotate-key-cron.sh >> /var/log/cron.log 2>&1
+```
+
+### Step 5: Test Manual Rotation (Optional)
+
+Before waiting for the monthly schedule, test the rotation manually:
+
+```bash
+# Run rotation script manually inside the container
+docker exec syshub-key-rotation-cron /app/docker/cron/rotate-key-cron.sh
+
+# Check the logs
+docker exec syshub-key-rotation-cron cat /var/log/cron.log
+
+# Verify API restarted
+docker-compose ps api
+```
+
+## 📅 Rotation Schedule
+
+**Current Schedule**: 1st of every month at 2:00 AM UTC
+
+To change the schedule, edit `docker/cron/crontab`:
+
+```cron
+# Every 90 days (recommended for production)
+0 2 1 */3 * /app/docker/cron/rotate-key-cron.sh >> /var/log/cron.log 2>&1
+
+# Every 30 days
+0 2 1 * * /app/docker/cron/rotate-key-cron.sh >> /var/log/cron.log 2>&1
+
+# Every Sunday at 3 AM (for testing)
+0 3 * * 0 /app/docker/cron/rotate-key-cron.sh >> /var/log/cron.log 2>&1
+```
+
+After changing, rebuild and restart:
+```bash
+docker-compose build key-rotation-cron
+docker-compose up -d key-rotation-cron
+```
+
+## 📊 Monitoring
+
+### View Cron Logs
+
+```bash
+# View cron execution log
+docker exec syshub-key-rotation-cron tail -f /var/log/cron.log
+
+# View rotation logs on host
+ls -lh logs/key-rotation/
+
+# View latest rotation log
+cat logs/key-rotation/key-rotation-*.log | tail -50
+```
+
+### View Rotation History
+
+```bash
+# View all rotation logs saved by the script
+ls -lh scripts/rotation-log-*.json
+
+# View latest rotation summary
+cat scripts/rotation-log-$(ls -t scripts/rotation-log-*.json | head -1)
+```
+
+### Check Next Scheduled Run
+
+```bash
+# Check when cron will run next
+docker exec syshub-key-rotation-cron date
+docker exec syshub-key-rotation-cron cat /etc/cron.d/key-rotation
+```
+
+## 🔔 Alerting (Optional)
+
+To get notified when rotations happen, modify `rotate-key-cron.sh` to send notifications:
+
+### Option 1: Email Notification
+
+```bash
+# Add to rotate-key-cron.sh after successful rotation
+echo "Key rotated successfully at $(date)" | \
+  mail -s "SysHub Key Rotation Success" admin@example.com
+```
+
+### Option 2: Slack Webhook
+
+```bash
+# Add to rotate-key-cron.sh after successful rotation
+curl -X POST -H 'Content-type: application/json' \
+  --data '{"text":"🔐 SysHub staging key rotated successfully"}' \
+  https://hooks.slack.com/services/YOUR/WEBHOOK/URL
+```
+
+### Option 3: Discord Webhook
+
+```bash
+# Add to rotate-key-cron.sh after successful rotation
+curl -H "Content-Type: application/json" \
+  -d '{"content":"🔐 SysHub staging key rotated successfully"}' \
+  https://discord.com/api/webhooks/YOUR/WEBHOOK
+```
+
+## 🛠️ Troubleshooting
+
+### Cron Container Not Running
+
+```bash
+# Check container status
+docker-compose ps key-rotation-cron
+
+# Check logs
+docker-compose logs key-rotation-cron
+
+# Restart container
+docker-compose restart key-rotation-cron
+```
+
+### Rotation Failed
+
+```bash
+# Check rotation logs
+docker exec syshub-key-rotation-cron cat /var/log/cron.log
+
+# Check script permissions
+docker exec syshub-key-rotation-cron ls -l /app/docker/cron/rotate-key-cron.sh
+
+# Run rotation manually for debugging
+docker exec syshub-key-rotation-cron sh -x /app/docker/cron/rotate-key-cron.sh
+```
+
+### API Not Restarting After Rotation
+
+```bash
+# Check if docker socket is mounted
+docker exec syshub-key-rotation-cron ls -l /var/run/docker.sock
+
+# Check if cron container can access docker
+docker exec syshub-key-rotation-cron docker ps
+
+# Manually restart API
+docker-compose restart api
+```
+
+### Permission Issues with .env.api
+
+```bash
+# Check .env.api permissions in container
+docker exec syshub-key-rotation-cron ls -l /app/.env
+
+# The volume should be mounted as :rw (read-write), not :ro
+# Verify in docker-compose.yml:
+# - .env.api:/app/.env:rw  ✅ Correct
+# - .env.api:/app/.env:ro  ❌ Wrong
+```
+
+## 🔐 Security Considerations
+
+### File Permissions
+
+- `.env.api` on host: `chmod 600` (owner read/write only)
+- `logs/key-rotation/`: `chmod 755` (owner full, others read)
+- Rotation logs contain key previews (first 20 chars), keep secure
+
+### Docker Socket Access
+
+The cron container needs access to `/var/run/docker.sock` to restart the API container. This is a privileged operation. Consider:
+
+1. **Network isolation**: The cron container is on the same network as API only
+2. **Read-only socket**: Mounted as `:ro` to prevent container creation
+3. **Minimal permissions**: Container only needs restart capability
+
+### Key Backup
+
+Before rotation, the script automatically:
+- Backs up `.env` to `.env.backup-[timestamp]`
+- Saves rotation log to `scripts/rotation-log-[timestamp].json`
+
+Keep these backups for audit trail and emergency recovery.
+
+## 📝 Maintenance
+
+### Update Cron Image
+
+When you update the API image, rebuild the cron image too:
+
+```bash
+docker-compose pull api
+docker-compose build --no-cache key-rotation-cron
+docker-compose up -d
+```
+
+### Clean Old Logs
+
+```bash
+# Remove rotation logs older than 90 days
+find logs/key-rotation/ -name "*.log" -mtime +90 -delete
+find scripts/ -name "rotation-log-*.json" -mtime +90 -delete
+
+# Remove old .env backups
+find . -name ".env.backup-*" -mtime +90 -delete
+```
+
+## 📞 Support
+
+- **Documentation**: `/docs/ENCRYPTION_KEY_MANAGEMENT.md`
+- **Quick Start**: `/docs/QUICK_START_KEY_MANAGEMENT.md`
+- **Rotation Logs**: `/scripts/rotation-log-*.json`
+- **Security Audit**: `/SECURITY_AUDIT_REPORT.md`
+
+## ✅ Verification Checklist
+
+After setup, verify:
+
+- [ ] Cron container is running (`docker-compose ps`)
+- [ ] Cron schedule is configured (`docker exec ... crontab -l`)
+- [ ] Log directory exists and is writable
+- [ ] `.env.api` is mounted as read-write in cron container
+- [ ] Docker socket is accessible from cron container
+- [ ] Manual test rotation succeeds
+- [ ] API restarts successfully after rotation
+- [ ] Rotation logs are created in `logs/key-rotation/`
+- [ ] 2FA verification still works after rotation
+
+---
+
+**Next Key Rotation**: 1st of next month at 2:00 AM UTC 🗓️
diff --git a/docker/cron/crontab b/docker/cron/crontab
new file mode 100644
index 0000000..0689670
--- /dev/null
+++ b/docker/cron/crontab
@@ -0,0 +1,8 @@
+# Encryption Key Rotation Schedule
+# Runs on the 1st day of every month at 2:00 AM UTC
+# Format: minute hour day month weekday command
+
+# Monthly key rotation (1st of month at 2 AM)
+0 2 1 * * /app/docker/cron/rotate-key-cron.sh >> /var/log/cron.log 2>&1
+
+# Keep an empty line at the end of the file
diff --git a/docker/cron/docker-compose.cron.yml b/docker/cron/docker-compose.cron.yml
new file mode 100644
index 0000000..6db93aa
--- /dev/null
+++ b/docker/cron/docker-compose.cron.yml
@@ -0,0 +1,39 @@
+# Add this service to your existing docker-compose.yml
+
+services:
+  # Existing api service (for reference)
+  api:
+    image: ghcr.io/syscoin/syshub-api:master
+    env_file:
+      - .env.api
+    volumes:
+      - .firebase-service-account.json:/app/.firebase-service-account.json:ro
+      - .env.api:/app/.env:ro
+    ports:
+      - 3001:3001
+    network_mode: bridge
+    extra_hosts:
+      - "host.docker.internal:host-gateway"
+
+  # NEW: Key rotation cron sidecar
+  key-rotation-cron:
+    build:
+      context: .
+      dockerfile: docker/cron/Dockerfile
+    container_name: syshub-key-rotation-cron
+    restart: unless-stopped
+    env_file:
+      - .env.api
+    volumes:
+      # Mount .env.api as read-write so rotation script can update it
+      - .env.api:/app/.env:rw
+      - .firebase-service-account.json:/app/.firebase-service-account.json:ro
+      # Mount docker socket to restart API container
+      - /var/run/docker.sock:/var/run/docker.sock:ro
+      # Persist rotation logs
+      - ./logs/key-rotation:/var/log:rw
+    network_mode: bridge
+    extra_hosts:
+      - "host.docker.internal:host-gateway"
+    depends_on:
+      - api
diff --git a/docker/cron/rotate-key-cron.sh b/docker/cron/rotate-key-cron.sh
new file mode 100755
index 0000000..ea3cefc
--- /dev/null
+++ b/docker/cron/rotate-key-cron.sh
@@ -0,0 +1,36 @@
+#!/bin/sh
+# Monthly Encryption Key Rotation Script
+# Runs via cron in sidecar container
+
+set -e
+
+LOG_FILE="/var/log/key-rotation-$(date +%Y%m%d-%H%M%S).log"
+
+echo "========================================"
+echo "Starting encryption key rotation"
+echo "Date: $(date)"
+echo "========================================"
+
+# Change to app directory
+cd /app
+
+# Run rotation script (--force to skip confirmation)
+if node scripts/rotate-encryption-key.js --force 2>&1 | tee "$LOG_FILE"; then
+  echo "✅ Key rotation completed successfully"
+
+  # Restart API container to load new key
+  echo "🔄 Restarting API container..."
+  if docker restart syshub-api-api-1 2>&1 | tee -a "$LOG_FILE"; then
+    echo "✅ API container restarted successfully"
+  else
+    echo "❌ Failed to restart API container"
+    exit 1
+  fi
+
+  echo "========================================"
+  echo "Key rotation completed at $(date)"
+  echo "========================================"
+else
+  echo "❌ Key rotation failed"
+  exit 1
+fi