iCloud Document/Desktop Disaster

Greetings fellow Power Users! I recently purchased a new 13" MBP AND I had to nuke and pave my iMac. I restored the MBP from a Time Machine backup and re-built the iMac from scratch.

Neither machine is properly syncing Documents and Desktop folders to iCloud Drive.

  • All other iCloud syncing is working (calendar, contacts, notes, iMessage, etc)
  • If I add a file to the desktop or document folder from an iOS devices, that file shows up on the Macs so things download to the Macs, but do not upload from the Macs.
  • I’ve tried signing out/back in and I have a case open with AppleCare, but it’s been over a month with no movement.

Any Power User moves to try? :slight_smile:

How long ago did you do this? And what speed connection do you have? I ask because I ran into something similar to this. It cleared itself up after awhile. It seemed the document part of iCloud sync’ing was tied up in other iCloud stuff like sync Photos. (I have a lot of data).

I did this recently too. It took 3-4 days for it to fully sync.

Check the iCloud > Desktop / Document folders for another sub-folder named desktop and/or documents.

This happens when you enable iCloud drive on multiple machines. iCloud drive will create a sub- desktop and/or document folder per machine.

Also, make sure all machines are on the latest version of MacOS!

No, that’s not it. It’s been that way for over a month. The little dotted cloud icon is next to everything. Photos finished within about a day. Good speed at home and the office.

Checked both of those, neither are the problem :slight_smile: Every document I drop in any are that should sync (Desktop, Document, or iCloud Drive) shows up with the dotted cloud icon and then it just never goes anywhere.

Did you click on it?

Good question. Yes, but clicking on it does nothing; no status popup.

Could the problem be the files? How much do you have? Possible to remove them all and re-add them, folder for folder?

I don’t think so. I’ve tried moving some of them out and back in and they do nothing.