For me iCloud drive does sometimes just not sync, and is stuck on something, you can see the status of sync in the iCloud Drive Finder icon. Closing all apps o

For me iCloud drive does sometimes just not sync, and is stuck on something, you can see the status of sync in the iCloud Drive Finder icon. Closing all apps on mac and iOS, and running "killall bird" (bird is ithe icloud sync service) sometimes fixes it.