Fix auto-update hang by force-exiting stuck PTY cleanup

When quitAndInstall fires, Squirrel's ShipIt sanity-checks that the
target app has actually exited before swapping the bundle. If any PTY
child (stuck claude, shell with background jobs) ignores SIGHUP, the
main process hangs draining the fd, Squirrel aborts, and the old
version relaunches. Later the zombie process crashes and macOS shows
the "unexpectedly quit" dialog.

- updater:quitAndInstall now SIGKILLs PTYs, strips the before-quit
  listener, kicks off ShipIt, and force-exits after 1.5s
- before-quit (Cmd+Q path) keeps the graceful SIGHUP but arms a 1.5s
  watchdog so a stuck child can't hang the process indefinitely
- pty-manager kill/killAll accept an optional signal and tolerate
  already-dead PTYs
- dev:debug script now watches the real dev userData dir
  (Harness (Dev)) and cleans up its tail on exit via trap

Co-Authored-By: Claude Opus 4.6 (1M context) <noreply@anthropic.com>

Author: frenchie4111

package.json

@@ -10,7 +10,7 @@
   "description": "Harness - manage multiple Claude Code instances across git worktrees",
   "scripts": {
     "dev": "electron-vite dev",
-    "dev:debug": "electron-vite dev & sleep 2 && tail -f ~/Library/Application\\ Support/harness/debug.log",
+    "dev:debug": "sh -c 'trap \"kill 0\" EXIT; tail -F \"$HOME/Library/Application Support/Harness (Dev)/debug.log\" & electron-vite dev'",
     "log": "tail -f ~/Library/Application\\ Support/harness/debug.log",
     "log:clear": "rm -f ~/Library/Application\\ Support/harness/debug.log",
     "build": "electron-vite build",

src/main/index.ts

@@ -636,7 +636,37 @@ function registerIpcHandlers(): void {
   })
 
   ipcMain.handle('updater:quitAndInstall', () => {
-    autoUpdater.quitAndInstall()
+    log('updater', 'quitAndInstall requested — cleaning up for fast exit')
+    try {
+      stopWatchingStatus?.()
+      stopWatchingStatus = null
+    } catch (err) {
+      log('updater', 'stopWatchingStatus failed', err instanceof Error ? err.message : String(err))
+    }
+    try {
+      ptyManager.killAll('SIGKILL')
+    } catch (err) {
+      log('updater', 'ptyManager.killAll failed', err instanceof Error ? err.message : String(err))
+    }
+    try {
+      sealAllActive()
+      saveConfigSync(config)
+    } catch (err) {
+      log('updater', 'final persistence failed', err instanceof Error ? err.message : String(err))
+    }
+
+    // Skip our before-quit handler — it's already been done above, and it can
+    // hang waiting for PTY fds to drain. We just want Squirrel to see us gone.
+    app.removeAllListeners('before-quit')
+
+    // Hard-exit fallback. If Squirrel/Electron's quit takes longer than ~1.5s,
+    // force-kill the process so ShipIt's "target still running" check passes.
+    setTimeout(() => {
+      log('updater', 'fallback app.exit(0) — Squirrel should take over')
+      app.exit(0)
+    }, 1500)
+
+    autoUpdater.quitAndInstall(true, false)
     return true
   })
 
@@ -842,9 +872,24 @@ app.on('window-all-closed', () => {
   }
 })
 
+let quitWatchdogArmed = false
 app.on('before-quit', () => {
   stopWatchingStatus?.()
+  stopWatchingStatus = null
   ptyManager.killAll()
   sealAllActive()
   saveConfigSync(config)
+
+  // Force-exit watchdog: if a PTY child (stuck claude / shell) won't die after
+  // SIGHUP, the main process can hang indefinitely draining fds. Give the
+  // graceful path ~1.5s, then hard-exit. electron-updater's ShipIt helper has
+  // already been spawned by this point if an update is pending, so force-exit
+  // is safe — ShipIt runs independently and swaps the bundle once we're gone.
+  if (!quitWatchdogArmed) {
+    quitWatchdogArmed = true
+    setTimeout(() => {
+      log('app', 'quit watchdog fired — force-exiting')
+      app.exit(0)
+    }, 1500).unref()
+  }
 })

src/main/pty-manager.ts

@@ -82,18 +82,22 @@ export class PtyManager {
     }
   }
 
-  kill(id: string): void {
-    log('pty', `kill id=${id}`)
+  kill(id: string, signal?: string): void {
+    log('pty', `kill id=${id}${signal ? ` signal=${signal}` : ''}`)
     const instance = this.ptys.get(id)
     if (instance) {
-      instance.pty.kill()
+      try {
+        instance.pty.kill(signal)
+      } catch {
+        // ignore — pty may already be dead
+      }
       this.ptys.delete(id)
     }
   }
 
-  killAll(): void {
+  killAll(signal?: string): void {
     for (const [id] of this.ptys) {
-      this.kill(id)
+      this.kill(id, signal)
     }
   }