From 55b33b4e6969b771643becd1f2cfd6420b10986a Mon Sep 17 00:00:00 2001
From: Peter Steinberger <steipete@gmail.com>
Date: Tue, 6 Jan 2026 01:40:15 +0000
Subject: [PATCH] fix: stop gmail watcher restart on bind error

---
 CHANGELOG.md                    |  1 +
 src/hooks/gmail-watcher.test.ts | 14 ++++++++++++++
 src/hooks/gmail-watcher.ts      | 21 ++++++++++++++++++++-
 3 files changed, 35 insertions(+), 1 deletion(-)
 create mode 100644 src/hooks/gmail-watcher.test.ts

diff --git a/CHANGELOG.md b/CHANGELOG.md
index 8c3c42610..7b29b4a0c 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -14,6 +14,7 @@
 - CLI: auto-migrate legacy config entries on command start (same behavior as gateway startup).
 - Auth: prioritize OAuth profiles but fall back to API keys when refresh fails; stored profiles now load without explicit auth order.
 - Docs: add group chat participation guidance to the AGENTS template.
+- Gmail: stop restart loop when `gog gmail watch serve` fails to bind (address already in use).
 - Linux: auto-attempt lingering during onboarding (try without sudo, fallback to sudo) and prompt on install/restart to keep the gateway alive after logout/idle. Thanks @tobiasbischoff for PR #237.
 - TUI: migrate key handling to the updated pi-tui Key matcher API.
 - Logging: redact sensitive tokens in verbose tool summaries by default (configurable patterns).
diff --git a/src/hooks/gmail-watcher.test.ts b/src/hooks/gmail-watcher.test.ts
new file mode 100644
index 000000000..aa16e4ad2
--- /dev/null
+++ b/src/hooks/gmail-watcher.test.ts
@@ -0,0 +1,14 @@
+import { describe, expect, it } from "vitest";
+import { isAddressInUseError } from "./gmail-watcher.js";
+
+describe("gmail watcher", () => {
+  it("detects address already in use errors", () => {
+    expect(
+      isAddressInUseError(
+        "listen tcp 127.0.0.1:8788: bind: address already in use",
+      ),
+    ).toBe(true);
+    expect(isAddressInUseError("EADDRINUSE: address already in use")).toBe(true);
+    expect(isAddressInUseError("some other error")).toBe(false);
+  });
+});
diff --git a/src/hooks/gmail-watcher.ts b/src/hooks/gmail-watcher.ts
index bd4e07969..0b3133066 100644
--- a/src/hooks/gmail-watcher.ts
+++ b/src/hooks/gmail-watcher.ts
@@ -20,6 +20,12 @@ import { ensureTailscaleEndpoint } from "./gmail-setup-utils.js";
 
 const log = createSubsystemLogger("gmail-watcher");
 
+const ADDRESS_IN_USE_RE = /address already in use|EADDRINUSE/i;
+
+export function isAddressInUseError(line: string): boolean {
+  return ADDRESS_IN_USE_RE.test(line);
+}
+
 let watcherProcess: ChildProcess | null = null;
 let renewInterval: ReturnType<typeof setInterval> | null = null;
 let shuttingDown = false;
@@ -61,6 +67,7 @@ async function startGmailWatch(
 function spawnGogServe(cfg: GmailHookRuntimeConfig): ChildProcess {
   const args = buildGogWatchServeArgs(cfg);
   log.info(`starting gog ${args.join(" ")}`);
+  let addressInUse = false;
 
   const child = spawn("gog", args, {
     stdio: ["ignore", "pipe", "pipe"],
@@ -74,7 +81,11 @@ function spawnGogServe(cfg: GmailHookRuntimeConfig): ChildProcess {
 
   child.stderr?.on("data", (data: Buffer) => {
     const line = data.toString().trim();
-    if (line) log.warn(`[gog] ${line}`);
+    if (!line) return;
+    if (isAddressInUseError(line)) {
+      addressInUse = true;
+    }
+    log.warn(`[gog] ${line}`);
   });
 
   child.on("error", (err) => {
@@ -83,6 +94,14 @@ function spawnGogServe(cfg: GmailHookRuntimeConfig): ChildProcess {
 
   child.on("exit", (code, signal) => {
     if (shuttingDown) return;
+    if (addressInUse) {
+      log.warn(
+        "gog serve failed to bind (address already in use); stopping restarts. " +
+          "Another watcher is likely running. Set CLAWDBOT_SKIP_GMAIL_WATCHER=1 or stop the other process.",
+      );
+      watcherProcess = null;
+      return;
+    }
     log.warn(`gog exited (code=${code}, signal=${signal}); restarting in 5s`);
     watcherProcess = null;
     setTimeout(() => {