diff --git a/decnet/templates/http/entrypoint.sh b/decnet/templates/http/entrypoint.sh
index c1705a11..aba79672 100644
--- a/decnet/templates/http/entrypoint.sh
+++ b/decnet/templates/http/entrypoint.sh
@@ -33,17 +33,20 @@ cat > /etc/caddy/Caddyfile <<EOF
 EOF
 
 python3 /opt/server.py &
+FLASK_PID=$!
 
 # Wait for Flask to be ready before handing off to Caddy
 python3 -c "
-import socket, time
-for _ in range(40):
+import socket, sys, time
+for _ in range(80):
     try:
         s = socket.create_connection(('127.0.0.1', 8080), timeout=0.25)
         s.close()
-        break
+        sys.exit(0)
     except OSError:
         time.sleep(0.1)
-"
+print('Flask did not bind to :8080 in time', file=sys.stderr)
+sys.exit(1)
+" || { echo 'Flask startup failed — aborting'; kill $FLASK_PID 2>/dev/null; exit 1; }
 
 exec caddy run --config /etc/caddy/Caddyfile
diff --git a/decnet/templates/https/entrypoint.sh b/decnet/templates/https/entrypoint.sh
index 4f8ba0cc..64e4a877 100644
--- a/decnet/templates/https/entrypoint.sh
+++ b/decnet/templates/https/entrypoint.sh
@@ -68,17 +68,20 @@ cat > /etc/caddy/Caddyfile <<EOF
 EOF
 
 python3 /opt/server.py &
+FLASK_PID=$!
 
 # Wait for Flask to be ready before handing off to Caddy
 python3 -c "
-import socket, time
-for _ in range(40):
+import socket, sys, time
+for _ in range(80):
     try:
         s = socket.create_connection(('127.0.0.1', 8080), timeout=0.25)
         s.close()
-        break
+        sys.exit(0)
     except OSError:
         time.sleep(0.1)
-"
+print('Flask did not bind to :8080 in time', file=sys.stderr)
+sys.exit(1)
+" || { echo 'Flask startup failed — aborting'; kill $FLASK_PID 2>/dev/null; exit 1; }
 
 exec caddy run --config /etc/caddy/Caddyfile