Fix watch depth limit being inert on Windows (path separator)

src/sidecar/__tests__/file-watcher.test.ts

@@ -1,4 +1,5 @@
 import { describe, it, expect, vi, beforeEach, afterEach } from 'vitest'
+import { join } from 'path'
 import Database from 'better-sqlite3'
 import { initTestDb } from '../../shared/__tests__/helpers/test-db'
 
@@ -176,3 +177,21 @@ describe('handleTrigger execution lock', () => {
     expect(state.cooldownUntil).toBeLessThanOrEqual(afterExec + _testing.POST_EXEC_COOLDOWN_MS)
   })
 })
+
+describe('watchRelativeDepth', () => {
+  const wp = join('root', 'watched')
+
+  it('treats a direct child as depth 1', () => {
+    expect(_testing.watchRelativeDepth(wp, join(wp, 'a.txt'))).toBe(1)
+  })
+
+  it('counts nested segments with the OS separator so the depth limit holds', () => {
+    // Within the limit (depth <= 2): not skipped.
+    expect(_testing.watchRelativeDepth(wp, join(wp, 'a')) > 2).toBe(false)
+    expect(_testing.watchRelativeDepth(wp, join(wp, 'a', 'b')) > 2).toBe(false)
+    // Deeper than 2: must exceed the limit. Splitting only on '/' regressed
+    // this on Windows (backslash paths counted as a single segment).
+    expect(_testing.watchRelativeDepth(wp, join(wp, 'a', 'b', 'c')) > 2).toBe(true)
+    expect(_testing.watchRelativeDepth(wp, join(wp, 'a', 'b', 'c', 'd.txt')) > 2).toBe(true)
+  })
+})

src/sidecar/file-watcher.ts

@@ -54,6 +54,13 @@ export function syncWatches(): void {
   syncWatchesWithDatabase()
 }
 
+// Number of path segments `filePath` is below `watchPath`. path.relative()
+// returns backslash-separated paths on Windows, so split on either separator
+// (splitting only on '/' makes the depth limit inert on Windows).
+function watchRelativeDepth(watchPath: string, filePath: string): number {
+  return relative(watchPath, filePath).split(/[/\\]/).length
+}
+
 function startWatch(watch: Watch): void {
   if (activeWatchers.has(watch.id)) return
   if (!watch.actionPrompt) {
@@ -76,11 +83,7 @@ function startWatch(watch: Watch): void {
       const filePath = isDir ? join(watch.path, filename) : watch.path
 
       // Limit depth to 1 (direct children + 1 level of subdirectories)
-      if (isDir) {
-        const rel = relative(watch.path, filePath)
-        const depth = rel.split('/').length
-        if (depth > 2) return
-      }
+      if (isDir && watchRelativeDepth(watch.path, filePath) > 2) return
 
       handleTrigger(watch.id, actionPrompt, filePath)
     })
@@ -157,6 +160,7 @@ export const _testing = {
   handleTrigger: (watchId: number, actionPrompt: string, filePath: string) =>
     handleTrigger(watchId, actionPrompt, filePath),
   getWatchExecState,
+  watchRelativeDepth,
   get lastTrigger() { return lastTrigger },
   get watchExecState() { return watchExecState },
   DEBOUNCE_MS,