It seems that it's a common issue but I couldn't find a resolution anywhere. My Documents folder in iCloud is constantly stuck on "Waiting to Upload".
When I navigate the directory structure in Documents to find the innermost directory that has this status, and after I temporarily delete it, the directories higher up in the tree still have those statuses.
MacBook Pro 16″, macOS 13.2
Hi _Mike_G,
Welcome to Apple Support Communities. We understand that you're having an issue with your iCloud Documents. We'd like to help.
Are using any other device with iCloud Drive on it? If you go to those devices, are you able seeing Waiting to Upload? Have you tried connecting to another network to run out an issue with communication? It's possible that it could be related to the network connection or speed.
If you're not finding anything there, we'd like to see if you can boot into safe mode to see if that helps get those files uploaded:
How to use safe mode
Determine whether you're using a Mac with Apple silicon, then follow the appropriate steps:
Apple silicon
1. Shut down your Mac.
2. Turn on your Mac and continue to press and hold the power button until you see the startup options window.
3. Select your startup disk, then press and hold the Shift key while clicking “Continue in Safe Mode.”
4. Log in to your Mac. You might be asked to log in again.
Intel processor
1. Turn on or restart your Mac, then immediately press and hold the Shift key as your Mac starts up.
2. Release the key when you see the login window, then log in to your Mac.
3. You might be asked to log in again. On either the first or second login window, you should see ”Safe Boot” in the upper-right corner of the window.
After you've completed those steps, this resource can tell you how to proceed if you continue to see this issue in safe mode or not: How to use safe mode on your Mac
Hope that helps.
Cheers!
iCloud Documents folder stuck on "Waiting to Upload"
