diff --git a/apps/x/packages/core/src/workspace/watcher.ts b/apps/x/packages/core/src/workspace/watcher.ts
index be7344c4..c50163d7 100644
--- a/apps/x/packages/core/src/workspace/watcher.ts
+++ b/apps/x/packages/core/src/workspace/watcher.ts
@@ -16,20 +16,20 @@ export type WorkspaceChangeCallback = (event: z.infer<typeof WorkspaceChangeEven
 // unboundedly with usage; chokidar v4 holds one OS watch handle per file, so
 // watching all of WorkDir exhausts the process fd limit (EMFILE crash) once
 // the workdir gets big enough.
-const WATCHED_ROOTS = [
+const WATCHED_DIR_ROOTS = [
   'knowledge',
   'bases',
   'inbox_lists',
   'gmail_sync',
   'calendar_sync',
   'bg-tasks',
-  'config/agent-schedule.json',
 ];
+const WATCHED_FILE_ROOTS = ['config/agent-schedule.json'];
 
 /**
  * Create a workspace watcher
- * Watches the user-facing workspace roots (WATCHED_ROOTS) recursively and
- * emits WorkDir-relative change events via callback.
+ * Watches the user-facing workspace roots (WATCHED_DIR_ROOTS / WATCHED_FILE_ROOTS)
+ * recursively and emits WorkDir-relative change events via callback.
  *
  * Returns a watcher instance that can be closed.
  * The watcher emits events immediately without debouncing.
@@ -40,7 +40,18 @@ export async function createWorkspaceWatcher(
 ): Promise<FSWatcher> {
   await ensureWorkspaceRoot();
 
-  const roots = WATCHED_ROOTS.map((rel) => path.join(WorkDir, rel));
+  // chokidar v4 never picks up a watched directory that doesn't exist yet
+  // (a missing file is fine as long as its parent dir exists), so create the
+  // roots up front — otherwise e.g. calendar_sync/ appearing after app start
+  // would stay invisible until restart.
+  for (const rel of WATCHED_DIR_ROOTS) {
+    await fs.mkdir(path.join(WorkDir, rel), { recursive: true });
+  }
+  for (const rel of WATCHED_FILE_ROOTS) {
+    await fs.mkdir(path.dirname(path.join(WorkDir, rel)), { recursive: true });
+  }
+
+  const roots = [...WATCHED_DIR_ROOTS, ...WATCHED_FILE_ROOTS].map((rel) => path.join(WorkDir, rel));
   const watcher = chokidar.watch(roots, {
     ignoreInitial: true,
     // knowledge/ is a git repo (version history) — its .git object store is