diff --git a/DEPLOYMENT.md b/DEPLOYMENT.md
index fc05c91..127c5dd 100644
--- a/DEPLOYMENT.md
+++ b/DEPLOYMENT.md
@@ -133,6 +133,44 @@ wrangler pages deploy dist --project-name=aicodebattle
 
 ## Monitoring
 
+### Health Endpoints
+
+The Worker API provides two health endpoints for monitoring:
+
+- **Liveness**: `GET /health` or `GET /api/health`
+  - Returns 200 if the worker process is running
+  - Use for Kubernetes liveness probes
+
+- **Readiness**: `GET /ready` or `GET /api/ready`
+  - Returns 200 if database is connected and ready
+  - Returns 503 if database is unavailable
+  - Use for Kubernetes readiness probes
+
+Example responses:
+
+```json
+// GET /health
+{
+  "success": true,
+  "data": {
+    "status": "healthy",
+    "timestamp": "2024-01-15T10:30:00.000Z"
+  }
+}
+
+// GET /ready (when healthy)
+{
+  "success": true,
+  "data": {
+    "status": "ready",
+    "database": "connected",
+    "timestamp": "2024-01-15T10:30:00.000Z"
+  }
+}
+```
+
+### Cloudflare Monitoring
+
 - Cloudflare Analytics: Available in Cloudflare dashboard
 - Worker Logs: `wrangler tail`
 - Container Logs: `docker-compose logs -f`
diff --git a/PROGRESS.md b/PROGRESS.md
index ba80d8b..9ab790a 100644
--- a/PROGRESS.md
+++ b/PROGRESS.md
@@ -25,20 +25,23 @@
   - Cloudflare setup instructions
   - Container deployment commands
   - Troubleshooting guide
-
-### Remaining Phase 6 Work
-
-- [ ] Cloudflare Pages project creation and deployment
 - [x] D1 database schema and migrations
   - Complete schema.sql with all tables from plan
   - Added: predictions, predictor_stats, map_votes, replay_feedback, series, series_games, seasons
   - Added evolution fields to bots table (evolved, island, generation, parent_ids)
   - Created migrations/0001_initial.sql for D1 migrations
   - Updated wrangler.toml with migrations_dir config
+- [x] Monitoring endpoints
+  - `/health` - Liveness probe (always returns 200)
+  - `/ready` - Readiness probe (checks database connectivity, returns 503 if unavailable)
+  - Documented in DEPLOYMENT.md
+
+### Remaining Phase 6 Work (requires Cloudflare account access)
+
+- [ ] Cloudflare Pages project creation and deployment
 - [ ] R2 bucket creation and custom domain
-- [ ] Worker API deployment via Wrangler
+- [ ] Worker API deployment via Wrangler (`wrangler deploy`)
 - [ ] DNS configuration
-- [ ] Monitoring setup
 
 ### Phase 5 Completed ✅
 
diff --git a/worker-api/src/index.ts b/worker-api/src/index.ts
index 6d7c14b..8b23a69 100644
--- a/worker-api/src/index.ts
+++ b/worker-api/src/index.ts
@@ -66,9 +66,54 @@ export default {
     };
 
     try {
-      // Health check
+      // Health check (liveness probe - always returns 200 if process is running)
       if (path === '/health' || path === '/api/health') {
-        return json({ success: true, data: { status: 'healthy' } });
+        return json({
+          success: true,
+          data: {
+            status: 'healthy',
+            timestamp: new Date().toISOString(),
+          },
+        });
+      }
+
+      // Readiness check (checks if service can handle requests)
+      if (path === '/ready' || path === '/api/ready') {
+        try {
+          // Test database connectivity
+          const dbResult = await env.DB.prepare('SELECT 1 as ok').first();
+          const dbHealthy = dbResult?.ok === 1;
+
+          if (!dbHealthy) {
+            return json({
+              success: false,
+              data: {
+                status: 'not_ready',
+                database: 'error',
+                timestamp: new Date().toISOString(),
+              },
+            }, 503);
+          }
+
+          return json({
+            success: true,
+            data: {
+              status: 'ready',
+              database: 'connected',
+              timestamp: new Date().toISOString(),
+            },
+          });
+        } catch (error) {
+          return json({
+            success: false,
+            data: {
+              status: 'not_ready',
+              database: 'error',
+              error: String(error),
+              timestamp: new Date().toISOString(),
+            },
+          }, 503);
+        }
       }
 
       // ============ Job Endpoints (require API key) ============