Syncing Contacts with the Apple iCloud

too long; didn’t read: Back up with Time Machine before syncing your contacts via iCloud. If iCloud wipes out your contacts, you can restore the ~/Library/Application Support/AddressBook/ folder to get them back.

I regularly use two MacOS devices and one iOS device. Considering who else already has my contacts, I figure it was time, for convenience’s sake, to use Apple’s iCloud to sync my contacts across the three devices.

I obviously not writing this article to inform the world that everything went smoothly.

• My desktop has the definitive list of contacts.
• My phone has a copy of these contacts, synced recently.
• My laptop has only a handful of contacts with only phone numbers.[1]

So how should I proceed?

Well, obviously, turn on syncing contacts to iCloud from the desktop, to “prime” the contacts with the definitive list. Then, turn on syncing from the laptop and phone. I didn’t expect any issues.

What did I get?

• When I turned on syncing on the desktop, it didn’t ask me anything. I didn’t think anything of it.
• When I turned on syncing on the laptop, it asked if I wanted to merge my contacts to the cloud. I assumed that this meant it was going to merge with the contacts that had already synced from the desktop. I didn’t expect any problems since the laptop contacts were duplicates of the existing contacts (names and phone numbers were already in the other list). At most, I figured I’d have to resolve an easy merge-conflict or two.
• The merge went seamlessly.
• However, I didn’t see any of the desktop contacts show up on the laptop, even after waiting what I felt was an appropriate period.
• Instead, when I looked at the desktop, I was greeted with a very short list of contacts—the list of contacts from the laptop, in fact.
• iCloud: You keep using that word “merge”; I don’t think it means what you think it means.
• iCloud leaned back and folded its hands, a job well-done. I had only the smallest possible list of contacts and all of my contacts I’d curated over two decades were gone.

Well, I’m not an idiot, so they weren’t really gone. But iCloud had made a bit of work for me. If this happens to you, you can get your contacts back by doing the following:

1. Focus the Finder.
2. Select the Go menu.
3. Hold ⌥ to show the Library folder in the menu; select it to open a new Finder window.
4. Browse to the ~/Library/Application Support/AddressBook/ folder
5. Enter the Time Machine (I used the icon in the menu bar.
6. Restore that folder to a previous version.
7. You should see your prior contacts appear in the Contacts application.

Syncing worked properly for me after that.

It’s still a mystery to me how this could have failed to work properly. Apple has enough engineers and syncing a few address-book items isn’t rocket science.