From 5ad27fa25f730309407d4af8de1a7f693c8f3e20 Mon Sep 17 00:00:00 2001
From: Peter Steinberger <steipete@gmail.com>
Date: Sun, 5 Apr 2026 18:20:19 +0100
Subject: [PATCH] fix: allow slower Windows gateway restart health

---
 src/cli/daemon-cli/restart-health.test.ts | 28 +++++++++++++++++++++++
 src/cli/daemon-cli/restart-health.ts      | 13 ++++++++++-
 2 files changed, 40 insertions(+), 1 deletion(-)

diff --git a/src/cli/daemon-cli/restart-health.test.ts b/src/cli/daemon-cli/restart-health.test.ts
index 24595639408..bc4a4d7c5db 100644
--- a/src/cli/daemon-cli/restart-health.test.ts
+++ b/src/cli/daemon-cli/restart-health.test.ts
@@ -278,6 +278,34 @@ describe("inspectGatewayRestart", () => {
     expect(sleep).toHaveBeenCalledTimes(25);
   });
 
+  it("waits longer before stopped-free early exit on Windows", async () => {
+    Object.defineProperty(process, "platform", { value: "win32", configurable: true });
+    const service = makeGatewayService({ status: "stopped" });
+    inspectPortUsage.mockResolvedValue({
+      port: 18789,
+      status: "free",
+      listeners: [],
+      hints: [],
+    });
+
+    const { waitForGatewayHealthyRestart } = await import("./restart-health.js");
+    const snapshot = await waitForGatewayHealthyRestart({
+      service,
+      port: 18789,
+      attempts: 120,
+      delayMs: 500,
+    });
+
+    expect(snapshot).toMatchObject({
+      healthy: false,
+      runtime: { status: "stopped" },
+      portUsage: { status: "free" },
+      waitOutcome: "stopped-free",
+      elapsedMs: 27_500,
+    });
+    expect(sleep).toHaveBeenCalledTimes(55);
+  });
+
   it("annotates timeout waits when the health loop exhausts all attempts", async () => {
     const service = makeGatewayService({ status: "running", pid: 8000 });
     inspectPortUsage.mockResolvedValue({
diff --git a/src/cli/daemon-cli/restart-health.ts b/src/cli/daemon-cli/restart-health.ts
index 6b94321d671..90e3b7fcd80 100644
--- a/src/cli/daemon-cli/restart-health.ts
+++ b/src/cli/daemon-cli/restart-health.ts
@@ -15,6 +15,8 @@ export const DEFAULT_RESTART_HEALTH_DELAY_MS = 500;
 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;
 
 export type GatewayRestartWaitOutcome = "healthy" | "stale-pids" | "stopped-free" | "timeout";
 
@@ -217,6 +219,12 @@ function shouldEarlyExitStoppedFree(
   );
 }
 
+function stoppedFreeEarlyExitGraceMs(): number {
+  return process.platform === "win32"
+    ? WINDOWS_STOPPED_FREE_EARLY_EXIT_GRACE_MS
+    : STOPPED_FREE_EARLY_EXIT_GRACE_MS;
+}
+
 function withWaitContext(
   snapshot: GatewayRestartSnapshot,
   waitOutcome: GatewayRestartWaitOutcome,
@@ -245,7 +253,10 @@ export async function waitForGatewayHealthyRestart(params: {
 
   let consecutiveStoppedFreeCount = 0;
   const STOPPED_FREE_THRESHOLD = 6;
-  const minAttemptForEarlyExit = Math.min(Math.ceil(10_000 / delayMs), Math.floor(attempts / 2));
+  const minAttemptForEarlyExit = Math.min(
+    Math.ceil(stoppedFreeEarlyExitGraceMs() / delayMs),
+    Math.floor(attempts / 2),
+  );
 
   for (let attempt = 0; attempt < attempts; attempt += 1) {
     if (snapshot.healthy) {