Fix Guide: Tahoe iCloud "Waiting to Upload" Desktop Fix

Symptom: Files on your macOS Tahoe Desktop or in the Documents folder show a cloud icon with "Waiting to upload" indefinitely.

Why this happens

The bird daemon (which handles iCloud Drive) can lose its file-monitor permissions, especially if the "Optimized Storage" setting is toggled during an active sync.

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Fix 1: Force Restart the Bird Daemon

1. Open Terminal.
2. Run:

killall bird

1. Wait 10 seconds for it to automatically restart.

Fix 2: Reset CloudDocs Metadata

1. In Terminal:

rm -rf ~/Library/Application\ Support/CloudDocs

1. Warning: This forces a full re-sync of your iCloud file list.

Recommended Tool: Gemini 2

If your iCloud is stuck due to thousands of duplicate files:

- Get Gemini 2 to clean up your Desktop and Documents folders, making it much easier for the bird daemon to finish the sync.