diff --git a/src/gateway/server-close.test.ts b/src/gateway/server-close.test.ts
index 04fa3580fc4d..d5e75b11acc5 100644
--- a/src/gateway/server-close.test.ts
+++ b/src/gateway/server-close.test.ts
@@ -182,6 +182,26 @@ describe("createGatewayCloseHandler", () => {
     }
   });
 
+  it("still runs later teardown when cron.stopAndDrain() rejects (no listener strand)", async () => {
+    const stopAndDrain = vi.fn().mockRejectedValue(new Error("stream watcher stop failed"));
+    const httpClose = vi.fn((cb: (err?: Error | null) => void) => cb(null));
+    const deps = createGatewayCloseTestDeps({
+      cron: { stop: vi.fn(), stopAndDrain } as never,
+      httpServer: { close: httpClose, closeIdleConnections: vi.fn() } as never,
+    });
+    const close = createGatewayCloseHandler(deps);
+
+    const result = await close({ reason: "test" });
+
+    // A rejecting stopAndDrain must be swallowed (recorded as a warning) and must NOT skip the
+    // remaining teardown -- otherwise the HTTP/WS listeners and timers strand and the next
+    // start hits EADDRINUSE.
+    expect(stopAndDrain).toHaveBeenCalledTimes(1);
+    expect(deps.heartbeatRunner.stop).toHaveBeenCalledTimes(1);
+    expect(httpClose).toHaveBeenCalled();
+    expect(result.warnings.length).toBeGreaterThan(0);
+  });
+
   it("completes a clean shutdown with a ShutdownResult", async () => {
     const deps = createGatewayCloseTestDeps();
     const close = createGatewayCloseHandler(deps);
diff --git a/src/gateway/server-close.ts b/src/gateway/server-close.ts
index a27f6d09477a..ee9a7b28c5e1 100644
--- a/src/gateway/server-close.ts
+++ b/src/gateway/server-close.ts
@@ -883,12 +883,12 @@ export function createGatewayCloseHandler(
       await measureCloseStep("gmail-watcher", () =>
         shutdownStep("gmail-watcher", () => stopGmailWatcherOnDemand(), warnings),
       );
-      if (params.cron.stopAndDrain) {
-        await params.cron.stopAndDrain();
-      } else {
-        params.cron.stop();
-      }
-      params.heartbeatRunner.stop();
+      await shutdownStep(
+        "cron",
+        () => (params.cron.stopAndDrain ? params.cron.stopAndDrain() : params.cron.stop()),
+        warnings,
+      );
+      await shutdownStep("heartbeat-runner", () => params.heartbeatRunner.stop(), warnings);
       await shutdownStep(
         "task-registry-maintenance",
         () => params.stopTaskRegistryMaintenance?.(),