diff --git a/.dockerignore b/.dockerignore
index 3a90052..f9e4ccb 100644
--- a/.dockerignore
+++ b/.dockerignore
@@ -52,9 +52,12 @@ docker-compose*.yml
 # Documentation
 README.md
 CLAUDE.md
+DEPLOY.md
+README.production.md
 
-# Nginx config
+# Reverse proxy configs
 nginx.conf.example
+Caddyfile.example
 
 # Frontend build output (not needed during image build)
 frontend/frontend/dist
diff --git a/CLAUDE.md b/CLAUDE.md
index 026adf4..0f1c9a9 100644
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -153,6 +153,12 @@ docker compose -f docker-compose.production.yml exec backend uv run flask db upg
 - Set `SESSION_COOKIE_SECURE=true` for HTTPS
 - Configure OIDC URLs to match your domain
 
+**Reverse Proxy:**
+- Example configurations provided: `nginx.conf.example` and `Caddyfile.example`
+- Caddy recommended for automatic HTTPS with Let's Encrypt
+- Nginx for more control and advanced configurations
+- See `README.production.md` for detailed setup instructions
+
 ## Architecture
 
 ### Application Factory Pattern
diff --git a/Caddyfile.example b/Caddyfile.example
new file mode 100644
index 0000000..ecb2c2e
--- /dev/null
+++ b/Caddyfile.example
@@ -0,0 +1,98 @@
+# Example Caddyfile for production deployment
+# Caddy automatically handles HTTPS with Let's Encrypt!
+
+# Basic configuration - Caddy handles SSL automatically
+trivia.torrtle.co {
+    # Reverse proxy to Flask app
+    reverse_proxy localhost:5001
+
+    # Increase client upload size for images (default is 10MB)
+    request_body {
+        max_size 10MB
+    }
+
+    # Enable compression
+    encode gzip zstd
+
+    # Logging
+    log {
+        output file /var/log/caddy/trivia.log
+        format json
+    }
+}
+
+# Alternative: More explicit configuration with WebSocket support
+# (Though Caddy handles WebSocket upgrades automatically)
+trivia.torrtle.co {
+    # Main reverse proxy
+    reverse_proxy localhost:5001 {
+        # Forward real client IP
+        header_up X-Real-IP {remote_host}
+        header_up X-Forwarded-For {remote_host}
+        header_up X-Forwarded-Proto {scheme}
+        header_up X-Forwarded-Host {host}
+
+        # Health check
+        health_uri /api/health
+        health_interval 30s
+        health_timeout 5s
+    }
+
+    # Upload size
+    request_body {
+        max_size 10MB
+    }
+
+    # Compression
+    encode gzip zstd
+
+    # Security headers
+    header {
+        # Enable HSTS
+        Strict-Transport-Security "max-age=31536000; includeSubDomains; preload"
+
+        # Prevent clickjacking
+        X-Frame-Options "SAMEORIGIN"
+
+        # XSS protection
+        X-Content-Type-Options "nosniff"
+
+        # Referrer policy
+        Referrer-Policy "strict-origin-when-cross-origin"
+    }
+
+    # Logging
+    log {
+        output file /var/log/caddy/trivia.log {
+            roll_size 100mb
+            roll_keep 5
+            roll_keep_for 720h
+        }
+        format json
+    }
+}
+
+# Optional: Expose Celery Flower monitoring on subdomain
+flower.torrtle.co {
+    reverse_proxy localhost:5555
+
+    # Optional: Basic auth for protection
+    basicauth {
+        admin $2a$14$Zkx19XLiW6VYouLHR5NmfOFU0z2GTNmpkT/5qqR4M5.laVvNFqEAa
+    }
+}
+
+# Optional: Redirect www to non-www
+www.trivia.torrtle.co {
+    redir https://trivia.torrtle.co{uri} permanent
+}
+
+# Optional: Development/staging environment on different subdomain
+staging.trivia.torrtle.co {
+    reverse_proxy localhost:5002
+
+    # Basic auth to protect staging
+    basicauth {
+        staging $2a$14$Zkx19XLiW6VYouLHR5NmfOFU0z2GTNmpkT/5qqR4M5.laVvNFqEAa
+    }
+}
diff --git a/DEPLOY.md b/DEPLOY.md
new file mode 100644
index 0000000..90e90d6
--- /dev/null
+++ b/DEPLOY.md
@@ -0,0 +1,125 @@
+# Quick Deploy Guide
+
+Minimal steps to deploy the trivia app to production with Caddy.
+
+## Prerequisites
+
+- Linux server with Docker and Docker Compose installed
+- Domain name pointing to your server (e.g., `trivia.torrtle.co` → your server IP)
+- Port 80 and 443 open in firewall
+
+## 5-Minute Deploy
+
+### 1. Clone and Configure
+
+```bash
+# Clone repository
+git clone <your-repo-url>
+cd trivia-thang
+
+# Configure environment
+cp .env.production.example .env.production
+nano .env.production  # Update with your values
+```
+
+**Required settings in `.env.production`:**
+```bash
+CORS_ORIGINS=https://trivia.torrtle.co
+OIDC_ISSUER=https://auth.torrtle.co
+OIDC_CLIENT_SECRET=your_secret_here
+OIDC_REDIRECT_URI=https://trivia.torrtle.co/api/auth/callback
+FRONTEND_URL=https://trivia.torrtle.co
+SESSION_COOKIE_SECURE=true
+```
+
+### 2. Start Application
+
+```bash
+# Build and start
+docker compose -f docker-compose.production.yml up -d
+
+# Initialize database
+docker compose -f docker-compose.production.yml exec backend uv run flask db upgrade
+```
+
+### 3. Setup Caddy (Automatic HTTPS)
+
+```bash
+# Install Caddy
+curl -1sLf 'https://dl.cloudsmith.io/public/caddy/stable/gpg.key' | sudo gpg --dearmor -o /usr/share/keyrings/caddy-stable-archive-keyring.gpg
+curl -1sLf 'https://dl.cloudsmith.io/public/caddy/stable/debian.deb.txt' | sudo tee /etc/apt/sources.list.d/caddy-stable.list
+sudo apt update && sudo apt install caddy
+
+# Create minimal Caddyfile
+sudo tee /etc/caddy/Caddyfile << 'EOF'
+trivia.torrtle.co {
+    reverse_proxy localhost:5001
+}
+EOF
+
+# Start Caddy
+sudo systemctl restart caddy
+```
+
+### 4. Done!
+
+Visit `https://trivia.torrtle.co` - Caddy automatically handles HTTPS!
+
+## Verify Deployment
+
+```bash
+# Check if app is running
+curl http://localhost:5001/api/health
+
+# Check Docker containers
+docker compose -f docker-compose.production.yml ps
+
+# View logs
+docker compose -f docker-compose.production.yml logs -f backend
+```
+
+## Common Commands
+
+```bash
+# Restart application
+docker compose -f docker-compose.production.yml restart
+
+# Update application
+git pull
+docker compose -f docker-compose.production.yml up -d --build
+
+# View logs
+docker compose -f docker-compose.production.yml logs -f
+
+# Stop application
+docker compose -f docker-compose.production.yml down
+```
+
+## Troubleshooting
+
+### Can't connect to HTTPS
+
+Check Caddy logs:
+```bash
+sudo journalctl -u caddy -f
+```
+
+Caddy needs ports 80 and 443 open for Let's Encrypt challenge.
+
+### WebSocket issues
+
+Ensure your domain's DNS is properly configured and Caddy is running. Caddy handles WebSocket upgrades automatically.
+
+### Database errors
+
+Run migrations:
+```bash
+docker compose -f docker-compose.production.yml exec backend uv run flask db upgrade
+```
+
+---
+
+For detailed documentation, see:
+- `README.production.md` - Full deployment guide
+- `Caddyfile.example` - Advanced Caddy configuration
+- `nginx.conf.example` - Alternative Nginx configuration
diff --git a/README.production.md b/README.production.md
index f9a0023..fbbc148 100644
--- a/README.production.md
+++ b/README.production.md
@@ -67,17 +67,49 @@ sudo nginx -t
 sudo systemctl reload nginx
 ```
 
-#### Option B: Caddy (Simpler)
+#### Option B: Caddy (Recommended - Automatic HTTPS!)
 
-Create `/etc/caddy/Caddyfile`:
+Caddy is simpler than Nginx and handles HTTPS automatically with Let's Encrypt.
 
+```bash
+# Install Caddy (if not already installed)
+# Ubuntu/Debian:
+sudo apt install -y debian-keyring debian-archive-keyring apt-transport-https
+curl -1sLf 'https://dl.cloudsmith.io/public/caddy/stable/gpg.key' | sudo gpg --dearmor -o /usr/share/keyrings/caddy-stable-archive-keyring.gpg
+curl -1sLf 'https://dl.cloudsmith.io/public/caddy/stable/debian.deb.txt' | sudo tee /etc/apt/sources.list.d/caddy-stable.list
+sudo apt update
+sudo apt install caddy
+
+# Copy and edit the example Caddyfile
+sudo cp Caddyfile.example /etc/caddy/Caddyfile
+
+# Update your domain in the Caddyfile
+sudo nano /etc/caddy/Caddyfile
+
+# Validate configuration
+caddy validate --config /etc/caddy/Caddyfile
+
+# Restart Caddy
+sudo systemctl restart caddy
+
+# Check status
+sudo systemctl status caddy
+```
+
+**Simple Caddyfile (minimal):**
 ```caddy
 trivia.torrtle.co {
     reverse_proxy localhost:5001
 }
 ```
 
-Caddy automatically handles HTTPS with Let's Encrypt!
+**That's it!** Caddy automatically:
+- Obtains SSL certificate from Let's Encrypt
+- Handles WebSocket upgrades
+- Redirects HTTP to HTTPS
+- Renews certificates automatically
+
+See `Caddyfile.example` for advanced configuration with security headers, logging, and optional features.
 
 ## Services