diff --git a/src/cli/gateway-cli/run-loop.ts b/src/cli/gateway-cli/run-loop.ts
index c6b7d5ea21e..684e0a65c16 100644
--- a/src/cli/gateway-cli/run-loop.ts
+++ b/src/cli/gateway-cli/run-loop.ts
@@ -106,7 +106,10 @@ export async function runGatewayLoop(params: {
     const forceExitMs = isRestart ? DRAIN_TIMEOUT_MS + SHUTDOWN_TIMEOUT_MS : SHUTDOWN_TIMEOUT_MS;
     const forceExitTimer = setTimeout(() => {
       gatewayLog.error("shutdown timed out; exiting without full cleanup");
-      exitProcess(0);
+      // Exit non-zero on restart timeout so launchd/systemd treats it as a
+      // failure and triggers a clean process restart instead of assuming the
+      // shutdown was intentional. Stop-timeout stays at 0 (graceful). (#36822)
+      exitProcess(isRestart ? 1 : 0);
     }, forceExitMs);
 
     void (async () => {