Desktop and Documents files to iCloud Drive does not turn on

rwright,

Thank you for clarifying. Let's test in safe mode to further isolate the issue.

These steps should guide you:

"Start up your Intel-based Mac in safe mode

1. Turn on or restart your Mac, then immediately press and hold the Shift key until you see the login window.
2. Log in to your Mac.
3. You might be asked to log in again.
4. On either the first or second login window, you should see “Safe Boot” in the menu bar."

Additional details can be found here: Start up your Mac in safe mode

This article can explain how safe mode can help in this situation: Use safe mode on your Mac

Let us know the results as well as if anything changes while trying these steps.

Cheers!

Hi rwright,

When Desktop and Documents is enabled, everything automatically stays up to date everywhere. Make sure you're following these steps from the article that you viewed prior to posting: Add your Desktop and Documents files to iCloud Drive

1. From your Mac, choose Apple menu  > System Settings. In macOS Monterey or earlier, choose Apple menu  > System Preferences.

2.  Click Apple ID, then click iCloud.

3. Make sure that iCloud Drive is turned on.

4. Next to iCloud Drive, click Options.

5. Choose Desktop & Documents Folders.

6. Click Done.

If the setting continues to toggle off on its own, try testing the issue in safe mode. This will start up your Mac so that it performs certain checks and prevents some software from automatically loading or opening, which could help narrow down the cause of the issue. This article will walk you through the steps: Use safe mode on your Mac

Regards.

Hi rwright,

Thank you for confirming that it also occurs in safe mode. Next, we recommend that you reach out to Apple Support directly to take a further look and provide additional steps towards a solution. Please reach out here:

Apple Support

Hope this helps!

Have a great day.