You probably don’t know that iCloud Drive didn’t sync some files until you need them and were sure you put them in there. Well, that’s Apple’s sync story ever since I started using .Mac a long time ago. It just never worked. With .Mac and iDisk it was way worse, they also had the option to sync items in the Dock etc. and it was always a mess, good thing they got rid of it.

iCloud Drive just sucks and there are little to no tools to debug things in the right way, or force a re-sync of files. This little rant about file syncing tools is still true, especially for iCloud Drive. It’s annoying.

Well, back to topic. A few things you can try, they probably won’t work in your case, they probably didn’t even work for me, and it’s just luck. If you need file syncing, just go with Dropbox, seriously. It’s too expensive, the UI/UX sucks, but so far it’s still the only reliable service out there.

Monitor iCloud Drive status

brctl monitor com.apple.CloudDocs | grep %

If you see stuff stuck at 95.0% or weird messages such as server edit to download (which to this day had only one google search result, hopefully this one will be the 2nd) you can try and go ahead and update the file/folder like so.

Solutions (or trial and error)

  1. open your Terminal
  2. go into iCloud Drive folder
cd ~/Library/Mobile\ Documents/com\~apple\~CloudDocs/

Now jump into the folder you’re having issues with (again, with the cd command, e.G. cd Downloads) and run this:

find . ! -path "*.icloud" -print0|xargs -0 touch

This might trigger a proper re-sync of the files, but chances are that you’re still seeing issues. What worked for me ultimately was to move the given folder out of iCloud Drive, wait a while (because Apple…) and move them back in there.

Man, this sucks.