fix(windows): resolve gcloud/gog/tailscale PATHEXT shims before spawn to fix ENOENT on Windows

Angfr95 · BradGroux · commit cdcbad03b5c2 · 2026-05-05T00:13:28.000-05:00
diff --git a/CHANGELOG.md b/CHANGELOG.md
@@ -67,6 +67,7 @@ Docs: https://docs.openclaw.ai
 ### Fixes
 
 - Update/restart: probe managed Gateway restarts with the service environment and add a Docker product lane that exercises candidate-owned `openclaw update --yes --json` restarts, so SecretRef-backed local gateway auth cannot regress behind mocked restart checks. Thanks @vincentkoc.
+- Webhooks/Gmail/Windows: resolve `gcloud`, `gog`, and `tailscale` PATH/PATHEXT shims before setup and watcher spawns, using the Windows-safe `.cmd` wrapper for long-lived `gog serve` processes. (#74881, fixes #54470) Thanks @Angfr95.
 - Plugins/install: honor the beta update channel for onboarding and doctor-managed plugin installs by requesting floating npm and ClawHub specs with `@beta` while keeping persistent install records on the catalog default. Thanks @vincentkoc.
 - WhatsApp/onboarding: canonicalize setup and pairing allowlist entries to WhatsApp's digit-only phone ids while still accepting E.164, JID, and `whatsapp:` inputs, so personal-phone allowlists match WhatsApp Web sender ids after setup. Thanks @vincentkoc.
 - Gateway/startup: load provider plugins that own explicitly configured image, video, or music generation defaults so generation tools become live after gateway restart instead of remaining catalog-only. Fixes #77244. Thanks @buyuangtampan, @Nikoxx99, and @vincentkoc.
diff --git a/src/hooks/gmail-ops.ts b/src/hooks/gmail-ops.ts
@@ -1,4 +1,5 @@
 import { spawn } from "node:child_process";
+import path from "node:path";
 import { formatCliCommand } from "../cli/command-format.js";
 import {
   getRuntimeConfig,
@@ -9,8 +10,11 @@ import {
   resolveGatewayPort,
   validateConfigObjectWithPlugins,
 } from "../config/config.js";
+import { resolveExecutable } from "../infra/executable-path.js";
+import { getWindowsInstallRoots } from "../infra/windows-install-roots.js";
 import { runCommandWithTimeout } from "../process/exec.js";
 import { defaultRuntime } from "../runtime.js";
+import { normalizeLowercaseStringOrEmpty } from "../shared/string-coerce.js";
 import { displayPath } from "../utils.js";
 import {
   ensureDependency,
@@ -75,6 +79,38 @@ export type GmailRunOptions = GmailCommonOptions & {
 };
 
 const DEFAULT_GMAIL_TOPIC_IAM_MEMBER = "serviceAccount:gmail-api-push@system.gserviceaccount.com";
+let gogBin: string | undefined;
+const WINDOWS_UNSAFE_CMD_CHARS_RE = /[&|<>^%\r\n]/;
+
+function escapeForCmdExe(arg: string): string {
+  if (WINDOWS_UNSAFE_CMD_CHARS_RE.test(arg)) {
+    throw new Error(`Unsafe Windows cmd.exe argument detected: ${JSON.stringify(arg)}`);
+  }
+  if (!arg.includes(" ") && !arg.includes('"')) {
+    return arg;
+  }
+  return `"${arg.replace(/"/g, '""')}"`;
+}
+
+function resolveGogServeInvocation(args: string[]): {
+  args: string[];
+  command: string;
+  windowsHide?: true;
+  windowsVerbatimArguments?: true;
+} {
+  const command = (gogBin ??= resolveExecutable("gog"));
+  const ext = normalizeLowercaseStringOrEmpty(path.extname(command));
+  if (process.platform !== "win32" || (ext !== ".cmd" && ext !== ".bat")) {
+    return { command, args, windowsHide: process.platform === "win32" ? true : undefined };
+  }
+  const cmdExe = path.win32.join(getWindowsInstallRoots().systemRoot, "System32", "cmd.exe");
+  return {
+    command: cmdExe,
+    args: ["/d", "/s", "/c", [command, ...args].map(escapeForCmdExe).join(" ")],
+    windowsHide: true,
+    windowsVerbatimArguments: true,
+  };
+}
 
 export async function runGmailSetup(opts: GmailSetupOptions) {
   await ensureDependency("gcloud", ["--cask", "gcloud-cli"]);
@@ -358,14 +394,19 @@ export async function runGmailService(opts: GmailRunOptions) {
 function spawnGogServe(cfg: GmailHookRuntimeConfig) {
   const args = buildGogWatchServeArgs(cfg);
   defaultRuntime.log(`Starting gog ${buildGogWatchServeLogArgs(cfg).join(" ")}`);
-  return spawn("gog", args, { stdio: "inherit" });
+  const invocation = resolveGogServeInvocation(args);
+  return spawn(invocation.command, invocation.args, {
+    stdio: "inherit",
+    windowsHide: invocation.windowsHide,
+    windowsVerbatimArguments: invocation.windowsVerbatimArguments,
+  });
 }
 
 async function startGmailWatch(
   cfg: Pick<GmailHookRuntimeConfig, "account" | "label" | "topic">,
   fatal = false,
 ) {
-  const args = ["gog", ...buildGogWatchStartArgs(cfg)];
+  const args = [(gogBin ??= resolveExecutable("gog")), ...buildGogWatchStartArgs(cfg)];
   const result = await runCommandWithTimeout(args, { timeoutMs: 120_000 });
   if (result.code !== 0) {
     const message = result.stderr || result.stdout || "gog watch start failed";
diff --git a/src/hooks/gmail-setup-utils.ts b/src/hooks/gmail-setup-utils.ts
@@ -2,11 +2,13 @@ import fs from "node:fs";
 import path from "node:path";
 import { hasBinary } from "../agents/skills.js";
 import { formatErrorMessage } from "../infra/errors.js";
+import { resolveExecutable } from "../infra/executable-path.js";
 import { runCommandWithTimeout, type SpawnResult } from "../process/exec.js";
 import { resolveUserPath } from "../utils.js";
 import { normalizeServePath } from "./gmail.js";
 
 let cachedPythonPath: string | null | undefined;
+let gcloudBin: string | undefined;
 const MAX_OUTPUT_CHARS = 800;
 
 export function resetGmailSetupUtilsCachesForTest(): void {
@@ -156,7 +158,7 @@ async function runGcloudCommand(
   args: string[],
   timeoutMs: number,
 ): Promise<Awaited<ReturnType<typeof runCommandWithTimeout>>> {
-  return await runCommandWithTimeout(["gcloud", ...args], {
+  return await runCommandWithTimeout([(gcloudBin ??= resolveExecutable("gcloud")), ...args], {
     timeoutMs,
     env: await gcloudEnv(),
   });
@@ -269,9 +271,10 @@ export async function ensureTailscaleEndpoint(params: {
     return "";
   }
 
+  const tailscaleBin = resolveExecutable("tailscale");
   const statusArgs = ["status", "--json"];
   const statusCommand = formatCommand("tailscale", statusArgs);
-  const status = await runCommandWithTimeout(["tailscale", ...statusArgs], {
+  const status = await runCommandWithTimeout([tailscaleBin, ...statusArgs], {
     timeoutMs: 30_000,
   });
   if (status.code !== 0) {
@@ -300,7 +303,7 @@ export async function ensureTailscaleEndpoint(params: {
   const pathArg = normalizeServePath(params.path);
   const funnelArgs = [params.mode, "--bg", "--set-path", pathArg, "--yes", target];
   const funnelCommand = formatCommand("tailscale", funnelArgs);
-  const funnelResult = await runCommandWithTimeout(["tailscale", ...funnelArgs], {
+  const funnelResult = await runCommandWithTimeout([tailscaleBin, ...funnelArgs], {
     timeoutMs: 30_000,
   });
   if (funnelResult.code !== 0) {
diff --git a/src/hooks/gmail-watcher.ts b/src/hooks/gmail-watcher.ts
@@ -6,10 +6,14 @@
  */
 
 import { type ChildProcess, spawn } from "node:child_process";
+import path from "node:path";
 import { hasBinary } from "../agents/skills.js";
 import type { OpenClawConfig } from "../config/types.openclaw.js";
+import { resolveExecutable } from "../infra/executable-path.js";
+import { getWindowsInstallRoots } from "../infra/windows-install-roots.js";
 import { createSubsystemLogger } from "../logging/subsystem.js";
 import { runCommandWithTimeout } from "../process/exec.js";
+import { normalizeLowercaseStringOrEmpty } from "../shared/string-coerce.js";
 import { ensureTailscaleEndpoint } from "./gmail-setup-utils.js";
 import { isAddressInUseError } from "./gmail-watcher-errors.js";
 import {
@@ -26,6 +30,38 @@ let watcherProcess: ChildProcess | null = null;
 let renewInterval: ReturnType<typeof setInterval> | null = null;
 let shuttingDown = false;
 let currentConfig: GmailHookRuntimeConfig | null = null;
+let gogBin: string | undefined;
+const WINDOWS_UNSAFE_CMD_CHARS_RE = /[&|<>^%\r\n]/;
+
+function escapeForCmdExe(arg: string): string {
+  if (WINDOWS_UNSAFE_CMD_CHARS_RE.test(arg)) {
+    throw new Error(`Unsafe Windows cmd.exe argument detected: ${JSON.stringify(arg)}`);
+  }
+  if (!arg.includes(" ") && !arg.includes('"')) {
+    return arg;
+  }
+  return `"${arg.replace(/"/g, '""')}"`;
+}
+
+function resolveGogServeInvocation(args: string[]): {
+  args: string[];
+  command: string;
+  windowsHide?: true;
+  windowsVerbatimArguments?: true;
+} {
+  const command = (gogBin ??= resolveExecutable("gog"));
+  const ext = normalizeLowercaseStringOrEmpty(path.extname(command));
+  if (process.platform !== "win32" || (ext !== ".cmd" && ext !== ".bat")) {
+    return { command, args, windowsHide: process.platform === "win32" ? true : undefined };
+  }
+  const cmdExe = path.win32.join(getWindowsInstallRoots().systemRoot, "System32", "cmd.exe");
+  return {
+    command: cmdExe,
+    args: ["/d", "/s", "/c", [command, ...args].map(escapeForCmdExe).join(" ")],
+    windowsHide: true,
+    windowsVerbatimArguments: true,
+  };
+}
 
 /**
  * Check if gog binary is available
@@ -40,7 +76,7 @@ function isGogAvailable(): boolean {
 async function startGmailWatch(
   cfg: Pick<GmailHookRuntimeConfig, "account" | "label" | "topic">,
 ): Promise<boolean> {
-  const args = ["gog", ...buildGogWatchStartArgs(cfg)];
+  const args = [(gogBin ??= resolveExecutable("gog")), ...buildGogWatchStartArgs(cfg)];
   try {
     const result = await runCommandWithTimeout(args, { timeoutMs: 120_000 });
     if (result.code !== 0) {
@@ -63,10 +99,13 @@ function spawnGogServe(cfg: GmailHookRuntimeConfig): ChildProcess {
   const args = buildGogWatchServeArgs(cfg);
   log.info(`starting gog ${buildGogWatchServeLogArgs(cfg).join(" ")}`);
   let addressInUse = false;
+  const invocation = resolveGogServeInvocation(args);
 
-  const child = spawn("gog", args, {
+  const child = spawn(invocation.command, invocation.args, {
     stdio: ["ignore", "pipe", "pipe"],
     detached: false,
+    windowsHide: invocation.windowsHide,
+    windowsVerbatimArguments: invocation.windowsVerbatimArguments,
   });
 
   child.stdout?.on("data", (data: Buffer) => {
diff --git a/src/infra/executable-path.test.ts b/src/infra/executable-path.test.ts
@@ -1,13 +1,22 @@
 import fs from "node:fs/promises";
 import path from "node:path";
-import { describe, expect, it } from "vitest";
+import { afterEach, describe, expect, it, vi } from "vitest";
 import { withTempDir } from "../test-helpers/temp-dir.js";
 import {
   isExecutableFile,
+  resolveExecutable,
   resolveExecutableFromPathEnv,
   resolveExecutablePath,
 } from "./executable-path.js";
 
+function restoreEnvValue(name: string, value: string | undefined): void {
+  if (value === undefined) {
+    delete process.env[name];
+  } else {
+    process.env[name] = value;
+  }
+}
+
 describe("executable path helpers", () => {
   it("detects executable files and rejects directories or non-executables", async () => {
     await withTempDir({ prefix: "openclaw-exec-path-" }, async (base) => {
@@ -95,3 +104,95 @@ describe("executable path helpers", () => {
     ).toBeUndefined();
   });
 });
+
+describe("resolveExecutable", () => {
+  afterEach(() => {
+    vi.restoreAllMocks();
+  });
+
+  it("returns cmd unchanged on non-Windows platforms", () => {
+    const platformSpy = vi.spyOn(process, "platform", "get").mockReturnValue("linux");
+    expect(resolveExecutable("gcloud")).toBe("gcloud");
+    platformSpy.mockRestore();
+  });
+
+  it("returns cmd unchanged when it already carries a known PATHEXT extension on Windows", () => {
+    const platformSpy = vi.spyOn(process, "platform", "get").mockReturnValue("win32");
+    expect(resolveExecutable("gcloud.cmd")).toBe("gcloud.cmd");
+    expect(resolveExecutable("gcloud.exe")).toBe("gcloud.exe");
+    expect(resolveExecutable("gcloud.bat")).toBe("gcloud.bat");
+    expect(resolveExecutable("gcloud.com")).toBe("gcloud.com");
+    platformSpy.mockRestore();
+  });
+
+  it("resolves to the first .cmd result from PATH on Windows without executing where.exe", async () => {
+    const platformSpy = vi.spyOn(process, "platform", "get").mockReturnValue("win32");
+    await withTempDir({ prefix: "openclaw-exec-path-" }, async (base) => {
+      const binDir = path.join(base, "bin");
+      await fs.mkdir(binDir, { recursive: true });
+      const cmdPath = path.join(binDir, "gcloud.cmd");
+      const exePath = path.join(binDir, "gcloud.exe");
+      await fs.writeFile(cmdPath, "@echo off\n", "utf8");
+      await fs.writeFile(exePath, "exe\n", "utf8");
+
+      const originalPath = process.env.PATH;
+      const originalPathext = process.env.PATHEXT;
+      process.env.PATH = binDir;
+      process.env.PATHEXT = ".EXE;.CMD;.BAT;.COM";
+      try {
+        expect(resolveExecutable("gcloud")).toBe(cmdPath);
+      } finally {
+        restoreEnvValue("PATH", originalPath);
+        restoreEnvValue("PATHEXT", originalPathext);
+      }
+    });
+    platformSpy.mockRestore();
+  });
+
+  it("falls back to .exe when no .cmd match exists on Windows", async () => {
+    const platformSpy = vi.spyOn(process, "platform", "get").mockReturnValue("win32");
+    await withTempDir({ prefix: "openclaw-exec-path-" }, async (base) => {
+      const binDir = path.join(base, "bin");
+      await fs.mkdir(binDir, { recursive: true });
+      const exePath = path.join(binDir, "tailscale.exe");
+      await fs.writeFile(exePath, "exe\n", "utf8");
+
+      const originalPath = process.env.PATH;
+      process.env.PATH = binDir;
+      try {
+        expect(resolveExecutable("tailscale")).toBe(exePath);
+      } finally {
+        restoreEnvValue("PATH", originalPath);
+      }
+    });
+    platformSpy.mockRestore();
+  });
+
+  it("falls back to first PATH result when no .cmd or .exe match exists on Windows", async () => {
+    const platformSpy = vi.spyOn(process, "platform", "get").mockReturnValue("win32");
+    await withTempDir({ prefix: "openclaw-exec-path-" }, async (base) => {
+      const binDir = path.join(base, "bin");
+      await fs.mkdir(binDir, { recursive: true });
+      const ps1Path = path.join(binDir, "gcloud.ps1");
+      await fs.writeFile(ps1Path, "Write-Output ok\n", "utf8");
+
+      const originalPath = process.env.PATH;
+      const originalPathext = process.env.PATHEXT;
+      process.env.PATH = binDir;
+      process.env.PATHEXT = ".PS1";
+      try {
+        expect(resolveExecutable("gcloud")).toBe(ps1Path);
+      } finally {
+        restoreEnvValue("PATH", originalPath);
+        restoreEnvValue("PATHEXT", originalPathext);
+      }
+    });
+    platformSpy.mockRestore();
+  });
+
+  it("returns original cmd when no PATH match exists on Windows", () => {
+    const platformSpy = vi.spyOn(process, "platform", "get").mockReturnValue("win32");
+    expect(resolveExecutable("gog")).toBe("gog");
+    platformSpy.mockRestore();
+  });
+});
diff --git a/src/infra/executable-path.ts b/src/infra/executable-path.ts
@@ -95,7 +95,8 @@ export function resolveExecutableFromPathEnv(
   pathEnv: string,
   env?: NodeJS.ProcessEnv,
 ): string | undefined {
-  const entries = pathEnv.split(path.delimiter).filter(Boolean);
+  const delimiter = process.platform === "win32" ? ";" : path.delimiter;
+  const entries = pathEnv.split(delimiter).filter(Boolean);
   const extensions = resolveWindowsExecutableExtensions(executable, env);
   for (const entry of entries) {
     for (const ext of extensions) {
@@ -123,3 +124,50 @@ export function resolveExecutablePath(
     options?.env?.PATH ?? options?.env?.Path ?? process.env.PATH ?? process.env.Path ?? "";
   return resolveExecutableFromPathEnv(candidate, envPath, options?.env);
 }
+
+const KNOWN_PATHEXT = new Set([".com", ".exe", ".bat", ".cmd"]);
+
+/**
+ * On Windows, resolves a bare command name to its full .cmd or .exe path by
+ * probing PATH/PATHEXT without executing another resolver. On non-Windows this
+ * is a no-op.
+ */
+export function resolveExecutable(cmd: string): string {
+  if (process.platform !== "win32") {
+    return cmd;
+  }
+  if (KNOWN_PATHEXT.has(normalizeLowercaseStringOrEmpty(path.extname(cmd)))) {
+    return cmd;
+  }
+
+  const envPath = process.env.PATH ?? process.env.Path ?? "";
+  const entries = envPath.split(";").filter(Boolean);
+  const extensions = resolveWindowsExecutableExtensions(cmd, process.env);
+  const matches: string[] = [];
+  for (const entry of entries) {
+    for (const ext of extensions) {
+      const candidate = path.join(entry, cmd + ext);
+      if (isExecutableFile(candidate)) {
+        matches.push(candidate);
+      }
+    }
+  }
+
+  const cmdMatch = matches.find(
+    (match) => normalizeLowercaseStringOrEmpty(path.extname(match)) === ".cmd",
+  );
+  if (cmdMatch) {
+    return cmdMatch;
+  }
+  const exeMatch = matches.find(
+    (match) => normalizeLowercaseStringOrEmpty(path.extname(match)) === ".exe",
+  );
+  if (exeMatch) {
+    return exeMatch;
+  }
+  if (matches[0]) {
+    return matches[0];
+  }
+
+  return cmd;
+}
