July 2021 .... the problem is still there... has someone actually found the root problem of this ? I tried everything: Reboot Rename Disable/Re-enable iCloud Compress ... In my case I have folders marked as "Waiting to upload". When I rename them or add .nosync and then rename them back I can see a progress indicator uploading the changes... and then the state goes back to "Waiting to upload". I have the impression that all the files are there (I only checked one folder with this error, but I have 300 GB of data in iCloud) but the status is always blocked. I'm considering moving to a different backup/cloud solution since I can't afford losing those files since I need them for my accountancy.