diff --git a/tools/keepalive.py b/tools/keepalive.py
index 5d639bb..f039f12 100644
--- a/tools/keepalive.py
+++ b/tools/keepalive.py
@@ -1,19 +1,41 @@
-"""Simple keepalive ping for Railway services."""
+"""Keepalive ping for Railway services. Retries on failure to handle cold starts."""
 import httpx
 import asyncio
+from datetime import datetime, timezone
 
 SERVICES = [
     "https://central-production.up.railway.app/health",
 ]
 
+# Retry config: 3 attempts, 15s between, 30s timeout per request
+MAX_RETRIES = 3
+RETRY_DELAY = 15
+REQUEST_TIMEOUT = 30
+
+
 async def ping():
-    async with httpx.AsyncClient(timeout=10) as client:
+    timestamp = datetime.now(timezone.utc).strftime("%Y-%m-%d %H:%M:%S UTC")
+    async with httpx.AsyncClient(timeout=REQUEST_TIMEOUT) as client:
         for url in SERVICES:
-            try:
-                resp = await client.get(url)
-                print(f"✓ {url}: {resp.status_code}")
-            except Exception as e:
-                print(f"✗ {url}: {e}")
+            success = False
+            for attempt in range(1, MAX_RETRIES + 1):
+                try:
+                    resp = await client.get(url)
+                    if resp.status_code == 200:
+                        print(f"[{timestamp}] ✓ {url}: {resp.status_code}")
+                        success = True
+                        break
+                    else:
+                        print(f"[{timestamp}] ⚠ {url}: {resp.status_code} (attempt {attempt}/{MAX_RETRIES})")
+                except Exception as e:
+                    print(f"[{timestamp}] ✗ {url}: {e} (attempt {attempt}/{MAX_RETRIES})")
+                
+                if attempt < MAX_RETRIES:
+                    await asyncio.sleep(RETRY_DELAY)
+            
+            if not success:
+                print(f"[{timestamp}] ❌ {url}: FAILED after {MAX_RETRIES} attempts")
+
 
 if __name__ == "__main__":
     asyncio.run(ping())