From 6cb87299524e32645aec2f26143fd6135fe35f66 Mon Sep 17 00:00:00 2001
From: Peter Steinberger <steipete@gmail.com>
Date: Fri, 13 Mar 2026 18:47:28 +0000
Subject: [PATCH] fix: harden windows gateway stop cleanup

---
 src/daemon/schtasks.stop.test.ts | 46 ++++++++++++++++++++++++++++++++
 src/daemon/schtasks.ts           | 36 +++++++++++++++++++++++--
 2 files changed, 80 insertions(+), 2 deletions(-)

diff --git a/src/daemon/schtasks.stop.test.ts b/src/daemon/schtasks.stop.test.ts
index d2d43de3ca2..8142ff0d839 100644
--- a/src/daemon/schtasks.stop.test.ts
+++ b/src/daemon/schtasks.stop.test.ts
@@ -121,6 +121,52 @@ describe("Scheduled Task stop/restart cleanup", () => {
     });
   });
 
+  it("force-kills remaining busy port listeners when the first stop pass does not free the port", async () => {
+    await withWindowsEnv(async ({ env }) => {
+      await writeGatewayScript(env);
+      schtasksResponses.push(
+        { code: 0, stdout: "", stderr: "" },
+        { code: 0, stdout: "", stderr: "" },
+        { code: 0, stdout: "", stderr: "" },
+      );
+      findVerifiedGatewayListenerPidsOnPortSync.mockReturnValue([4242]);
+      inspectPortUsage.mockResolvedValueOnce({
+        port: 18789,
+        status: "busy",
+        listeners: [{ pid: 4242, command: "node.exe" }],
+        hints: [],
+      });
+      for (let i = 0; i < 20; i += 1) {
+        inspectPortUsage.mockResolvedValueOnce({
+          port: 18789,
+          status: "busy",
+          listeners: [{ pid: 4242, command: "node.exe" }],
+          hints: [],
+        });
+      }
+      inspectPortUsage
+        .mockResolvedValueOnce({
+          port: 18789,
+          status: "busy",
+          listeners: [{ pid: 5252, command: "node.exe" }],
+          hints: [],
+        })
+        .mockResolvedValueOnce({
+          port: 18789,
+          status: "free",
+          listeners: [],
+          hints: [],
+        });
+
+      const stdout = new PassThrough();
+      await stopScheduledTask({ env, stdout });
+
+      expect(killProcessTree).toHaveBeenNthCalledWith(1, 4242, { graceMs: 300 });
+      expect(killProcessTree).toHaveBeenNthCalledWith(2, expect.any(Number), { graceMs: 300 });
+      expect(inspectPortUsage.mock.calls.length).toBeGreaterThanOrEqual(22);
+    });
+  });
+
   it("falls back to inspected gateway listeners when sync verification misses on Windows", async () => {
     await withWindowsEnv(async ({ env }) => {
       await writeGatewayScript(env);
diff --git a/src/daemon/schtasks.ts b/src/daemon/schtasks.ts
index fcd8b08b1af..3a92f0944fc 100644
--- a/src/daemon/schtasks.ts
+++ b/src/daemon/schtasks.ts
@@ -463,6 +463,24 @@ async function waitForGatewayPortRelease(port: number, timeoutMs = 5_000): Promi
   return false;
 }
 
+async function terminateBusyPortListeners(port: number): Promise<number[]> {
+  const diagnostics = await inspectPortUsage(port).catch(() => null);
+  if (diagnostics?.status !== "busy") {
+    return [];
+  }
+  const pids = Array.from(
+    new Set(
+      diagnostics.listeners
+        .map((listener) => listener.pid)
+        .filter((pid): pid is number => Number.isFinite(pid) && pid > 0),
+    ),
+  );
+  for (const pid of pids) {
+    await terminateGatewayProcessTree(pid, 300);
+  }
+  return pids;
+}
+
 async function resolveFallbackRuntime(env: GatewayServiceEnv): Promise<GatewayServiceRuntime> {
   const port = resolveConfiguredGatewayPort(env);
   if (!port) {
@@ -655,7 +673,14 @@ export async function stopScheduledTask({ stdout, env }: GatewayServiceControlAr
   await terminateScheduledTaskGatewayListeners(effectiveEnv);
   await terminateInstalledStartupRuntime(effectiveEnv);
   if (stopPort) {
-    await waitForGatewayPortRelease(stopPort);
+    const released = await waitForGatewayPortRelease(stopPort);
+    if (!released) {
+      await terminateBusyPortListeners(stopPort);
+      const releasedAfterForce = await waitForGatewayPortRelease(stopPort, 2_000);
+      if (!releasedAfterForce) {
+        throw new Error(`gateway port ${stopPort} is still busy after stop`);
+      }
+    }
   }
   stdout.write(`${formatLine("Stopped Scheduled Task", taskName)}\n`);
 }
@@ -684,7 +709,14 @@ export async function restartScheduledTask({
   await terminateScheduledTaskGatewayListeners(effectiveEnv);
   await terminateInstalledStartupRuntime(effectiveEnv);
   if (restartPort) {
-    await waitForGatewayPortRelease(restartPort);
+    const released = await waitForGatewayPortRelease(restartPort);
+    if (!released) {
+      await terminateBusyPortListeners(restartPort);
+      const releasedAfterForce = await waitForGatewayPortRelease(restartPort, 2_000);
+      if (!releasedAfterForce) {
+        throw new Error(`gateway port ${restartPort} is still busy before restart`);
+      }
+    }
   }
   const res = await execSchtasks(["/Run", "/TN", taskName]);
   if (res.code !== 0) {