test: harden Parallels fresh install smoke

src/cli/daemon-cli/lifecycle.test.ts

@@ -39,17 +39,16 @@ const resolveGatewayPort = vi.hoisted(() => vi.fn((_cfg?: unknown, _env?: unknow
 const findVerifiedGatewayListenerPidsOnPortSync = vi.fn<(port: number) => number[]>(() => []);
 const signalVerifiedGatewayPidSync = vi.fn<(pid: number, signal: "SIGTERM" | "SIGUSR1") => void>();
 const formatGatewayPidList = vi.fn<(pids: number[]) => string>((pids) => pids.join(", "));
-const probeGateway =
-  vi.fn<
-    (opts: {
-      url: string;
-      auth?: { token?: string; password?: string };
-      timeoutMs: number;
-    }) => Promise<{
-      ok: boolean;
-      configSnapshot: unknown;
-    }>
-  >();
+const probeGateway = vi.fn<
+  (opts: {
+    url: string;
+    auth?: { token?: string; password?: string };
+    timeoutMs: number;
+  }) => Promise<{
+    ok: boolean;
+    configSnapshot: unknown;
+  }>
+>();
 const isRestartEnabled = vi.fn<(config?: { commands?: unknown }) => boolean>(() => true);
 const loadConfig = vi.hoisted(() => vi.fn(() => ({})));
 const recoverInstalledLaunchAgent = vi.hoisted(() => vi.fn());
@@ -290,6 +289,27 @@ describe("runDaemonRestart health checks", () => {
     expect(renderRestartDiagnostics).toHaveBeenCalledTimes(1);
   });
 
+  it("waits longer for Windows gateway restart health", async () => {
+    vi.spyOn(process, "platform", "get").mockReturnValue("win32");
+    waitForGatewayHealthyRestart.mockResolvedValue({
+      healthy: true,
+      staleGatewayPids: [],
+      runtime: { status: "running" },
+      portUsage: { port: 18789, status: "busy", listeners: [], hints: [] },
+    });
+
+    await runDaemonRestart({ json: true });
+
+    expect(waitForGatewayHealthyRestart).toHaveBeenCalledWith(
+      expect.objectContaining({
+        attempts: 360,
+        delayMs: 500,
+        includeUnknownListenersAsStale: true,
+        port: 18789,
+      }),
+    );
+  });
+
   it("fails restart with a stopped-free message when the waiter exits early", async () => {
     const { formatCliCommand } = await import("../command-format.js");
     const unhealthy: RestartHealthSnapshot = {

src/cli/daemon-cli/lifecycle.ts

@@ -33,6 +33,13 @@ import type { DaemonLifecycleOptions } from "./types.js";
 
 const POST_RESTART_HEALTH_ATTEMPTS = DEFAULT_RESTART_HEALTH_ATTEMPTS;
 const POST_RESTART_HEALTH_DELAY_MS = DEFAULT_RESTART_HEALTH_DELAY_MS;
+const WINDOWS_POST_RESTART_HEALTH_TIMEOUT_MS = 180_000;
+
+function postRestartHealthAttempts(): number {
+  return process.platform === "win32"
+    ? Math.ceil(WINDOWS_POST_RESTART_HEALTH_TIMEOUT_MS / POST_RESTART_HEALTH_DELAY_MS)
+    : POST_RESTART_HEALTH_ATTEMPTS;
+}
 
 function formatRestartFailure(params: {
   health: GatewayRestartSnapshot;
@@ -183,7 +190,8 @@ export async function runDaemonRestart(opts: DaemonLifecycleOptions = {}): Promi
   const restartPort = await resolveGatewayLifecyclePort(service).catch(() =>
     resolveGatewayPortFallback(),
   );
-  const restartWaitMs = POST_RESTART_HEALTH_ATTEMPTS * POST_RESTART_HEALTH_DELAY_MS;
+  const restartHealthAttempts = postRestartHealthAttempts();
+  const restartWaitMs = restartHealthAttempts * POST_RESTART_HEALTH_DELAY_MS;
   const restartWaitSeconds = Math.round(restartWaitMs / 1000);
 
   return await runServiceRestart({
@@ -204,7 +212,7 @@ export async function runDaemonRestart(opts: DaemonLifecycleOptions = {}): Promi
       if (restartedWithoutServiceManager) {
         const health = await waitForGatewayHealthyListener({
           port: restartPort,
-          attempts: POST_RESTART_HEALTH_ATTEMPTS,
+          attempts: restartHealthAttempts,
           delayMs: POST_RESTART_HEALTH_DELAY_MS,
         });
         if (health.healthy) {
@@ -233,7 +241,7 @@ export async function runDaemonRestart(opts: DaemonLifecycleOptions = {}): Promi
       let health = await waitForGatewayHealthyRestart({
         service,
         port: restartPort,
-        attempts: POST_RESTART_HEALTH_ATTEMPTS,
+        attempts: restartHealthAttempts,
         delayMs: POST_RESTART_HEALTH_DELAY_MS,
         includeUnknownListenersAsStale: process.platform === "win32",
       });
@@ -254,7 +262,7 @@ export async function runDaemonRestart(opts: DaemonLifecycleOptions = {}): Promi
         health = await waitForGatewayHealthyRestart({
           service,
           port: restartPort,
-          attempts: POST_RESTART_HEALTH_ATTEMPTS,
+          attempts: restartHealthAttempts,
           delayMs: POST_RESTART_HEALTH_DELAY_MS,
           includeUnknownListenersAsStale: process.platform === "win32",
         });

src/cli/daemon-cli/restart-health.test.ts

@@ -89,6 +89,7 @@ async function inspectAmbiguousOwnershipWithProbe(
 }
 
 async function waitForStoppedFreeGatewayRestart() {
+  const attempts = process.platform === "win32" ? 360 : 120;
   const service = makeGatewayService({ status: "stopped" });
   inspectPortUsage.mockResolvedValue({
     port: 18789,
@@ -101,7 +102,7 @@ async function waitForStoppedFreeGatewayRestart() {
   return waitForGatewayHealthyRestart({
     service,
     port: 18789,
-    attempts: 120,
+    attempts,
     delayMs: 500,
   });
 }
@@ -292,9 +293,9 @@ describe("inspectGatewayRestart", () => {
       runtime: { status: "stopped" },
       portUsage: { status: "free" },
       waitOutcome: "stopped-free",
-      elapsedMs: 27_500,
+      elapsedMs: 92_500,
     });
-    expect(sleep).toHaveBeenCalledTimes(55);
+    expect(sleep).toHaveBeenCalledTimes(185);
   });
 
   it("annotates timeout waits when the health loop exhausts all attempts", async () => {

src/cli/daemon-cli/restart-health.ts

@@ -20,7 +20,7 @@ export const DEFAULT_RESTART_HEALTH_ATTEMPTS = Math.ceil(
   DEFAULT_RESTART_HEALTH_TIMEOUT_MS / DEFAULT_RESTART_HEALTH_DELAY_MS,
 );
 const STOPPED_FREE_EARLY_EXIT_GRACE_MS = 10_000;
-const WINDOWS_STOPPED_FREE_EARLY_EXIT_GRACE_MS = 25_000;
+const WINDOWS_STOPPED_FREE_EARLY_EXIT_GRACE_MS = 90_000;
 
 export type GatewayRestartWaitOutcome = "healthy" | "stale-pids" | "stopped-free" | "timeout";