I just picked up a 2015 MacBook Air off Craigslist. Previous owner had reinstalled El Capitan on it. I went ahead and installed Catalina and opted into my accounts. My Photos synced fine but my documents and desktop from iCloud hasn’t synced. If I go into finder nothing shows in iCloud Drive. I created a file in the Documents folder but it doesn’t appear on iCloud. Everything else iCloud related seems to be fine, Keychain, Safari bookmarks, mail, etc. Can’t find any setting that seems out of place. Any ideas? Other machines syncing to iCloud run High Sierra due to age.
Try adding some files to iCloud rather than a folder. If they don’t start syncing within an hour or so uncheck iCloud Drive, wait a few minutes, then select it again.
I’ve found that occasionally iCloud requires some “encouragement” to get things moving.
Turned off iCloud Drive again then back on. Have Activity Monitor running and nsurlsessiond is receiving a modest amount of data. Few hundred meg so far and steadily receiving. Nothing showing in finder yet but it is showing the little empty cloud icon indicating it needs to update. I’ll just let it run for a few hours.
May slow down later since the new season of Lucifer just dropped today on Netflix.
And items are showing up on the desktop and in the documents folder. We’ll seek how long it takes as my connection is an AT&T hotspot.