I’ve run into a serious problem, and I’m posting a description of it here on the off change that somebody might be able to help.
I have created and/or modified files on my new iPad Pro 12.9”, but all these files refuse to sync to iCloud Drive showing only ‘Waiting to Upload’ status in the Files App. Files created/modified on my other devices (MacBook Air, iPad Pro 10.5”, iPhone X) synchronise without any problems and also appear on the problematic iPad. This issue started around a week ago with no apparent cause.
I searched the Net and found that this is a long-standing issue with iCloud with no apparent remedy. I have tried all thing suggested online: shutting down, restarting, switching the iCloud Drive off and on again – all this to no avail. Eventually I even erased all content and settings; actually, I did this several times, sometimes restoring from iCloud backup, sometimes setting up the device as a new iPad, but always the files created or modified on the iPad refused to sync and showed the ‘Waiting to Upload’ status. In all these efforts I used my main Apple ID.
I then, as a debugging experiment, tried to setup the iPad with a different account/Apple ID, and lo and behold: everything worked as expected with files syncing up to iCloud Drive as soon as they were created/saved/modified.
So, the problem seems to be with my Apple account. As I don’t know what else to try, I have now scheduled an Apple support call for next Tuesday (too busy tomorrow) and hope to get help from them.
The problematic setup:
iPad Pro 12.9”, running iOS 12.2 latest public beta (NB! The problem started already with 12.1. and I downloaded the beta hoping it might offer a fix.)