diff --git a/src/main/native-chat/transcript-watch-liveness.test.ts b/src/main/native-chat/transcript-watch-liveness.test.ts
index 84be20dde58..8667f58af08 100644
--- a/src/main/native-chat/transcript-watch-liveness.test.ts
+++ b/src/main/native-chat/transcript-watch-liveness.test.ts
@@ -60,7 +60,8 @@ function claudeLine(uuid: string, role: 'user' | 'assistant', text: string): str
   })}\n`
 }
 
-async function waitFor(predicate: () => boolean, timeoutMs = 2_000): Promise<void> {
+// fs.watch and filesystem mutations use the platform clock; poll observable callbacks to a deadline.
+async function waitFor(predicate: () => boolean, timeoutMs = 5_000): Promise<void> {
   const start = Date.now()
   while (!predicate()) {
     if (Date.now() - start > timeoutMs) {
@@ -166,13 +167,14 @@ describe('native chat transcript watcher liveness', () => {
       onReplace: replacements,
       onAppend: () => {},
       debounceMs: 0,
-      reconciliationIntervalMs: 20
+      reconciliationIntervalMs: 10_000
     })
     await waitFor(() => snapshots.mock.calls.length === 1)
 
     await writeFile(filePath, prefixAfter + stableTail)
     const future = new Date(Date.now() + 10_000)
     await utimes(filePath, future, future)
+    watchCallbacks[0]!('change', 'transcript.jsonl')
     await waitFor(() =>
       replacements.mock.calls.flat(2).some((message) => message.id === 'prefix-new')
     )
diff --git a/src/main/windows/windows-host-job.win32.test.ts b/src/main/windows/windows-host-job.win32.test.ts
index ceba9ab6f14..94e9c323860 100644
--- a/src/main/windows/windows-host-job.win32.test.ts
+++ b/src/main/windows/windows-host-job.win32.test.ts
@@ -30,6 +30,18 @@ function isAlive(pid: number): boolean {
   }
 }
 
+// Job-object teardown is external to fake timers; poll the real process table to a deadline.
+async function waitForProcessExit(pid: number, timeoutMs: number): Promise<boolean> {
+  const deadline = Date.now() + timeoutMs
+  while (Date.now() < deadline) {
+    if (!isAlive(pid)) {
+      return true
+    }
+    await sleep(50)
+  }
+  return !isAlive(pid)
+}
+
 describeOnWindows('host job reaps the tree when the host dies', () => {
   let dir: string
 
@@ -83,11 +95,13 @@ describeOnWindows('host job reaps the tree when the host dies', () => {
     // Force-kill only the host: no tree kill, nothing given a chance to unwind.
     // This is the daemon-crash shape.
     process.kill(host.pid!, 'SIGKILL')
-    await sleep(3_000)
-
     try {
-      expect(isAlive(shellPid)).toBe(false)
-      expect(isAlive(grandchildPid)).toBe(false)
+      const [shellExited, grandchildExited] = await Promise.all([
+        waitForProcessExit(shellPid, 15_000),
+        waitForProcessExit(grandchildPid, 15_000)
+      ])
+      expect(shellExited).toBe(true)
+      expect(grandchildExited).toBe(true)
     } finally {
       for (const pid of [shellPid, grandchildPid]) {
         try {