Howdy FrankTME - This worked. Albeit a little heavy handed. I had previously tried to shut off iCloud Drive and allowed it to build a local cache in my user folder. That way I had all of the files that "were there" before i did much else. That is located in your ~/iCloud Drive (Archive) folder. I then issued you command but with the /. added to it so it looked like: sudo killall bird; sudo rm -rf ~/Library/Mobile\ Documents/com~apple~CloudDocs; sudo killall bird It wiped out all of the individual files but left the folders (as far as I can tell) intact. As I moved files into the iCloud Drive again, the sync started to work. Thank you for your suggestion! Chris