diff --git a/src/main/ipc/parcel-watcher-child-termination.ts b/src/main/ipc/parcel-watcher-child-termination.ts
index d4376468574..fc498410438 100644
--- a/src/main/ipc/parcel-watcher-child-termination.ts
+++ b/src/main/ipc/parcel-watcher-child-termination.ts
@@ -28,7 +28,9 @@ export class WatcherTerminationQueue {
   private current: Promise<void> | null = null
 
   waitFor<T>(operation: () => Promise<T>): Promise<T> | null {
-    return this.current?.then(operation) ?? null
+    // Why: an idle child may miss its exit deadline without poisoning the
+    // reusable supervisor; queued work must re-check state after either result.
+    return this.current?.then(operation, operation) ?? null
   }
 
   getCurrent(): Promise<void> | null {
diff --git a/src/main/ipc/parcel-watcher-unsubscribe-timeout.test.ts b/src/main/ipc/parcel-watcher-unsubscribe-timeout.test.ts
index b028a13bf92..2aad68d54b7 100644
--- a/src/main/ipc/parcel-watcher-unsubscribe-timeout.test.ts
+++ b/src/main/ipc/parcel-watcher-unsubscribe-timeout.test.ts
@@ -120,6 +120,38 @@ describe('watcher native unsubscribe timeout', () => {
     }
   })
 
+  it('spawns a fresh child for a subscribe queued before an idle exit deadline miss', async () => {
+    vi.useFakeTimers()
+    try {
+      const promise = subscribeViaWatcherProcess('/repo', vi.fn(), {})
+      const first = currentChild()
+      ackSubscribe(first, 0)
+      const subscription = await promise
+
+      const unsubscribe = subscription.unsubscribe().catch((error: unknown) => error)
+      const queued = subscribeViaWatcherProcess('/repo2', vi.fn(), {})
+
+      await vi.advanceTimersByTimeAsync(WATCHER_PROCESS_EXIT_DEADLINE_MS)
+      const error = (await unsubscribe) as Error & { physicalExit?: Promise<void> }
+      expect(error).toMatchObject({
+        message: 'file watcher process did not exit after termination deadline',
+        physicalExit: expect.any(Promise)
+      })
+
+      expect(forkMock).toHaveBeenCalledTimes(2)
+      const second = currentChild()
+      expect(second.sent[0]).toMatchObject({ op: 'subscribe', dir: '/repo2' })
+      ackSubscribe(second)
+      await expect(queued).resolves.toMatchObject({ unsubscribe: expect.any(Function) })
+
+      first.emit('exit', null, 'SIGKILL')
+      await error.physicalExit
+      expect(vi.getTimerCount()).toBe(0)
+    } finally {
+      vi.useRealTimers()
+    }
+  })
+
   it('rejects only after an unkillable child reaches its exit deadline', async () => {
     vi.useFakeTimers()
     try {
diff --git a/src/shared/cross-platform-path.test.ts b/src/shared/cross-platform-path.test.ts
index 4098e8f9b86..70d313ba63c 100644
--- a/src/shared/cross-platform-path.test.ts
+++ b/src/shared/cross-platform-path.test.ts
@@ -19,6 +19,7 @@ describe('cross-platform path containment', () => {
     expect(normalizeRuntimePathForComparison('/srv/team\\repo')).toBe('/srv/team\\repo')
     expect(normalizeRuntimePathForComparison('/srv/team/repo')).toBe('/srv/team/repo')
     expect(isPathInsideOrEqual('/srv/team\\repo', '/srv/team/repo/file.ts')).toBe(false)
+    expect(relativePathInsideRoot('/srv/repo', '/srv/repo/a\\b.txt')).toBe('a\\b.txt')
   })
 
   it('handles Windows drive roots and sibling drives case-insensitively', () => {
diff --git a/src/shared/cross-platform-path.ts b/src/shared/cross-platform-path.ts
index fee96842af8..e329784719b 100644
--- a/src/shared/cross-platform-path.ts
+++ b/src/shared/cross-platform-path.ts
@@ -69,7 +69,9 @@ export function isPathInsideOrEqual(rootPath: string, candidatePath: string): bo
 
 export function relativePathInsideRoot(rootPath: string, candidatePath: string): string | null {
   const normalizedCandidate = trimRuntimePathTrailingSlash(
-    normalizeRuntimePathSeparators(candidatePath)
+    isWindowsAbsolutePathLike(candidatePath)
+      ? normalizeRuntimePathSeparators(candidatePath)
+      : candidatePath.replace(/\/+/g, '/')
   )
   const comparisonRoot = normalizeRuntimePathForComparison(rootPath)
   const comparisonCandidate = normalizeRuntimePathForComparison(candidatePath)