My wife has the exact same problem — though she probably has closer to 100 groups. Every now and then, the groups on iCloud.com will appear to be empty. I’ve tried restoring from a backup after turning off sync, and that worked. Today, I tried something else.
Logged in on her account on the Mac, I also opened up her contacts in iCloud and looked at the first empty group. I then went to the Contacts app in macOS and found the same group. I edited the group name on the Mac (as simple as adding a space or a period to the end), and waited a few seconds, et voilà, the contacts suddenly appeared in the group in iCloud. Next group, same thing.
Lather, rinse, repeat.
NB: don’t do this backwards; if you rename a group that’s empty, all your devices will get the empty group, not the one with contacts!
It appears to be a sync bug in iCloud, where the group name doesn’t line up with some other index. Changing the name forces a resync, which resolves the index problem.
This could probably be AppleScript-ed, but I can’t see a way to create a Shortcut to do it on iOS/iPadOS as Shortcuts doesn’t grok groups. It would be great if there were a way to easily resync all the groups at once.
Any ideas?
11-17-2020 10:18 PM