Problem with iCloud Drive "Desktop and Documents folder" check box not sticking
Later today I actually solved it. Mostly by chance. What I did was that I changed the computer name via Preferences -&gt; Sharing -&gt; Computer name:
I did anyway want to change it and after I changed it and checked the terminal I noticed some folder name change in my home directory.
So after this I again tried to check the Preferences -&gt; Apple ID -&gt; iCloud Drive , Options ... -&gt; &quot;Desktop and Documents Folders&quot; box, and this time it took longer for the spinning wheel and it worked. After allowing it to sync for 10 min and then a quick reboot I not have the desktop and documents folders under the iCloud Drive section in Finder and it is synced with all my precious documents and devices.