From 697087f2eba75b25ae57ee32c4a86337efd125ed Mon Sep 17 00:00:00 2001
From: Teknium <127238744+teknium1@users.noreply.github.com>
Date: Wed, 26 Aug 2026 07:53:20 -0700
Subject: [PATCH] fix(desktop): SIGKILL-escalate the owned SSH backend when it
 survives the graceful quit wait (#91668 remainder)
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The #95085 quit teardown kills the owned serve --isolated before the
SSH tunnel closes, but a backend mid-turn (in-flight LLM call, live MCP
children) can ride out SIGTERM past cleanupStale's 5s graceful wait.
The old code then gave up (threw, kept the lockfile) and before-quit's
6s race closed SSH anyway — reparenting the still-running serve to
pid 1: the reported leak, now specific to quit-during-active-turn.
Escalate to kill -9 with a confirmed-exit wait; only an unkillable pid
(D-state, permissions) still throws and preserves the lock record so
the next connect's reap pass retries.
---
 .../desktop/electron/remote-lifecycle.test.ts | 49 +++++++++++++++++++
 apps/desktop/electron/remote-lifecycle.ts     | 26 ++++++++--
 2 files changed, 70 insertions(+), 5 deletions(-)

diff --git a/apps/desktop/electron/remote-lifecycle.test.ts b/apps/desktop/electron/remote-lifecycle.test.ts
index bfe7d89891..832be8836a 100644
--- a/apps/desktop/electron/remote-lifecycle.test.ts
+++ b/apps/desktop/electron/remote-lifecycle.test.ts
@@ -1365,3 +1365,52 @@ test('remote SSH ownership capability requires both secure bootstrap flags', asy
   const unsupported = fakeSsh([[/serve --help/, 'NO\n']])
   assert.equal(await remoteSupportsSshOwnership(unsupported, '/x/hermes'), false)
 })
+
+test('cleanupStale escalates to SIGKILL when the backend survives the graceful wait (#91668 quit-during-active-turn)', async () => {
+  // A serve mid-turn (in-flight LLM call, live MCP children) can ride out
+  // SIGTERM well past the 5s graceful wait. Before-quit races the whole
+  // teardown against 6s and then closes SSH — so a give-up here reparents
+  // the still-running backend to pid 1: exactly the #91668 leak. The
+  // graceful-wait failure must escalate to SIGKILL and still drop the lock.
+  const ssh = fakeSsh([
+    [/print\("OWNED"/, 'OWNED\n'],
+    [(cmd: string) => /kill 9 &&/.test(cmd), new Error('exit 1: pid alive after graceful wait')]
+  ])
+
+  await cleanupStale(ssh, OWNERSHIP_ID, {
+    pid: 9,
+    spawnNonce: SPAWN_NONCE,
+    hermesPath: '/x/hermes',
+    logPath: spawnLogPath(OWNERSHIP_ID, SPAWN_NONCE)
+  })
+
+  assert.ok(
+    ssh.calls.some(c => /kill -9 9\b/.test(c)),
+    'must escalate to SIGKILL after the graceful wait fails'
+  )
+  assert.ok(
+    ssh.calls.some(c => /rm -f .*backend\.lock\.json/.test(c)),
+    'lockfile must still be dropped after the forced kill'
+  )
+})
+
+test('cleanupStale keeps the lockfile when even SIGKILL cannot confirm the pid died', async () => {
+  const ssh = fakeSsh([
+    [/print\("OWNED"/, 'OWNED\n'],
+    [(cmd: string) => /kill 9 &&/.test(cmd), new Error('exit 1: pid alive after graceful wait')],
+    [(cmd: string) => /kill -9 9\b/.test(cmd), new Error('exit 1: unkillable (D-state)')]
+  ])
+
+  await assert.rejects(
+    cleanupStale(ssh, OWNERSHIP_ID, {
+      pid: 9,
+      spawnNonce: SPAWN_NONCE,
+      hermesPath: '/x/hermes',
+      logPath: spawnLogPath(OWNERSHIP_ID, SPAWN_NONCE)
+    }),
+    /Could not terminate/
+  )
+
+  // The record must survive so the next connect's reap pass retries.
+  assert.ok(!ssh.calls.some(c => /rm -f .*backend\.lock\.json/.test(c)))
+})
diff --git a/apps/desktop/electron/remote-lifecycle.ts b/apps/desktop/electron/remote-lifecycle.ts
index fbc4b5cf25..b671de2b3d 100644
--- a/apps/desktop/electron/remote-lifecycle.ts
+++ b/apps/desktop/electron/remote-lifecycle.ts
@@ -506,11 +506,27 @@ async function cleanupStale(ssh, ownershipId, lock, pidAlive = true) {
       ).trim()
 
       void result
-    } catch (cause) {
-      const error: any = new Error('Could not terminate the stale SSH backend.')
-      error.kind = 'transient-transport-error'
-      error.cause = cause
-      throw error
+    } catch {
+      // A backend mid-turn (in-flight LLM call, live MCP children) can ride
+      // out SIGTERM past the 5s graceful wait — and before-quit races this
+      // whole teardown against 6s before closing SSH, so giving up here
+      // reparents the still-running serve to pid 1: the #91668 leak, now on
+      // the quit-during-active-turn path. Escalate to SIGKILL and require a
+      // confirmed exit before treating the record as reclaimed.
+      try {
+        await ssh.exec(
+          `kill -9 ${Number(lock.pid)} 2>/dev/null; ` +
+            `i=0; while kill -0 ${Number(lock.pid)} 2>/dev/null; do ` +
+            `i=$((i+1)); [ "$i" -ge 20 ] && exit 1; sleep 0.1; done`
+        )
+      } catch (cause) {
+        // Even SIGKILL could not confirm death (D-state, permissions). Keep
+        // the lockfile so the next connect's reap pass retries.
+        const error: any = new Error('Could not terminate the stale SSH backend.')
+        error.kind = 'transient-transport-error'
+        error.cause = cause
+        throw error
+      }
     }
   }