diff --git a/DEPLOYMENT-CHECKLIST.md b/DEPLOYMENT-CHECKLIST.md
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+# Deployment Checklist - Oliver Metadata Tool v4.0
+
+## ✅ Pre-Deployment
+
+### 1. Backend .env Configuration
+```bash
+cd /opt/solventum-image-metadata
+sudo cp .env.production .env
+sudo nano .env
+```
+
+**Required variables:**
+```env
+SECRET_KEY=<generate-with-python-secrets>
+OPENAI_API_KEY=sk-...
+AZURE_CLIENT_SECRET=<your-secret>
+```
+
+**Verify Azure AD settings:**
+```env
+AZURE_CLIENT_ID=9079054c-9620-4757-a256-23413042f1ef
+AZURE_TENANT_ID=e519c2e6-bc6d-4fdf-8d9c-923c2f002385
+REDIRECT_URI=https://ai-sandbox.oliver.solutions/solventum-image-metadata/
+```
+
+### 2. Apache Configuration
+
+Add to `/etc/apache2/sites-available/solventum-image-metadata.conf`:
+
+```apache
+# Frontend - static files
+Alias /solventum-image-metadata /var/www/html/solventum-image-metadata
+
+<Directory /var/www/html/solventum-image-metadata>
+    Options -Indexes +FollowSymLinks
+    AllowOverride All
+    Require all granted
+
+    RewriteEngine On
+    RewriteBase /solventum-image-metadata
+    RewriteCond %{REQUEST_FILENAME} !-f
+    RewriteCond %{REQUEST_FILENAME} !-d
+    RewriteCond %{REQUEST_URI} !^/solventum-image-metadata/api/
+    RewriteRule ^ /solventum-image-metadata/index.html [L]
+</Directory>
+
+# Backend API
+ProxyPass /solventum-image-metadata/api/ http://localhost:5001/
+ProxyPassReverse /solventum-image-metadata/api/ http://localhost:5001/
+ProxyTimeout 600
+```
+
+Enable modules:
+```bash
+sudo a2enmod rewrite alias proxy proxy_http
+sudo apache2ctl configtest
+sudo systemctl reload apache2
+```
+
+## ✅ Deployment
+
+```bash
+cd /opt/solventum-image-metadata
+git pull origin main
+sudo ./deploy.sh
+```
+
+## ✅ Verification
+
+### 1. Check Backend
+```bash
+curl http://localhost:5001/health
+# Expected: {"status":"healthy"}
+```
+
+### 2. Check Frontend
+```bash
+curl https://ai-sandbox.oliver.solutions/solventum-image-metadata/
+# Expected: HTML with React app
+```
+
+### 3. Check API through Apache
+```bash
+curl https://ai-sandbox.oliver.solutions/solventum-image-metadata/api/health
+# Expected: {"status":"healthy"}
+```
+
+### 4. Test SSO
+1. Go to: https://ai-sandbox.oliver.solutions/solventum-image-metadata/
+2. Click "Login with Microsoft"
+3. Should redirect to Azure AD
+4. After login, should return to dashboard
+
+### 5. Test File Upload
+1. Login to dashboard
+2. Select "Manual Entry" or "AI Generation"
+3. Drag & drop a PDF file
+4. Edit metadata (title, subject, keywords)
+5. Click "Save Metadata"
+6. Download file
+7. Verify: `exiftool downloaded.pdf`
+
+## 📊 Final Status
+
+- [ ] Backend running on port 5001
+- [ ] Redis running in Docker
+- [ ] Frontend deployed to /var/www/html/solventum-image-metadata
+- [ ] Apache configured with Alias and ProxyPass
+- [ ] .env configured with all secrets
+- [ ] SSO redirect to Azure AD working
+- [ ] SSO callback to dashboard working
+- [ ] File upload working
+- [ ] Metadata editing working
+- [ ] Download working
+
+## 🆘 Troubleshooting
+
+### Backend not starting
+```bash
+docker logs oliver-backend --tail 100
+```
+
+### Frontend 404
+```bash
+ls -la /var/www/html/solventum-image-metadata/
+# Should contain: index.html, assets/, etc.
+```
+
+### SSO redirect loop
+```bash
+# Check .env REDIRECT_URI matches Azure AD exactly
+grep REDIRECT_URI /opt/solventum-image-metadata/.env
+# Must be: https://ai-sandbox.oliver.solutions/solventum-image-metadata/
+```
+
+### API 404 errors
+```bash
+# Check Apache proxy
+sudo apache2ctl -S | grep solventum
+# Check backend is running
+curl http://localhost:5001/docs
+```
diff --git a/frontend/.env.production b/frontend/.env.production
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+# Frontend Production Environment
+# API requests go through Apache proxy
+VITE_API_URL=/api