Why can't I sync Desktop & Documents folders?

I’ve finally started getting around to clearing out my OneDrive external storage and have been trying to migrate everything to iCloud via my Documents folder. Although I have the 2TB iCloud for my family, it is less than 25% used, so I have plenty of room to accommodate the ~200GB of data in my Docs folder. However, when I click the appropriate switch, it immediately switches back off.

Any ideas?

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I’ve never used this feature but I found a discussion about this problem.

https://discussions.apple.com/thread/255061132?sortBy=rank

Does your iCloud Drive already have Desktop and Documents folders? That might be the problem but I would make sure I have a good backup then contact Apple Support on how to proceed.

I wonder if OneDrive is stopping you from being able to turn on Desktop & Documents sync.

From the Apple support page:

If you want to store your files in iCloud Drive and another cloud storage service, you can keep copies of your files in both, but you can’t keep folders from a third-party cloud service in iCloud Drive. You can keep your other cloud service folders in a different place on your Mac, like the home folder.
If you already use a feature from another cloud provider that syncs or manages your Desktop and Documents folders, you need to turn it off to use Desktop and Documents.

This doesn’t really explain how the Desktop and Documents feature might know about other sync services, but I wouldn’t be surprised if something has detected the presence of OneDrive.

From:

Have you tried signing out and back in to iCloud ?

I use OneDrive purely as a remote drive, not as a sync service. The app doesn’t exist on my mac.

I ended up doing the usual unscientific Apple method of problem solving: when logic fails, start flipping switches on and off, logging in and out, and rebooting. I tend to mistakenly search for a specific, technical reason for an issue rather than remember the advice I give to all the volunteer operators at the church AV department that I run: “When in doubt, reboot.”

I did something, and now it works. Curiously though, it renamed my Documents folder to “Documents - MacBook Pro” and put the handful of work files on my desktop into a folder (on my desktop) named “Desktop - MacBook Pro.” In doing so, my ScanSnap was unable to find it’s “Save to” folder. I haven’t used too many other apps since, so I haven’t gotten any other error messages due to the folder name changes… yet.

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My weird suggestion is to wait. It might do nothing, but with iCloud, it might do something?

I’ve synced my Desktop and Documents folder via iCloud for several years now without “issues,” but with a handful of weird occurrences like this.