Ask a Mac: Calendar, Contacts Swallowed by the Cloud

What to do when iCal and iPhone have irreconcilable differences?

What’s Wrong?

Yipes! My iPhone’s calendar and contacts have stopped syncing with my MobileMe calendar and contacts. I’ve tried deleting my MobileMe account on my iPhone, then re-creating it to force the iPhone to sync properly with MobileMe. My mail synced OK but my calendar events and contacts have disappeared. They’re safe on my computers and on MobileMe itself but they just won’t sync with the iPhone. Help!

What to Do

One of the best selling points of Apple’s cloud solution, MobileMe, is how easily and transparently it syncs your mail, calendar, contacts and Safari bookmarks among all your computers and iDevices. Occasionally, however, it succumbs to hiccups like this one, where it refuses to sync properly.

You’ve done the thing you ought to do — re-creating your MobileMe account on your iPhone — and still you have no joy. Short of the cumbersome fixes (re-installing iTunes, restoring your iPhone from a backup — assuming those tactics would even work), here’s what has worked for some people:

Re-setting your Push settings. The objective of this solution is to “force” your iPhone to sync manually with MobileMe in hopes that your data will be restored to your phone.

1. On your iPhone go to Settings » Mail, Contacts, Calendars » Fetch New Data. Turn Off Push.
2. Set Fetch to Manually.
3. Go back one screen to Accounts, select your MobileMe account and click the red Delete Account button.
4. Back on the Accounts screen, select Add Account… and re-create your MobileMe account. Make sure you set Mail, Contacts and Calendars to On (Bookmarks, Notes and Find My iPhone are up to you).
5. Go back to Fetch New Data and turn Push back on.
6. Open your Mail or Contacts app. If all goes well, you’ll see them re-appear.

It didn’t work! What do I do now?

Re-setting your sync data. Here’s your other option; this one is your best bet, though a tad more complicated.

1. Make sure your Mac has synced very recently with MobileMe, and that it has the most recent Mail, Contacts and Calendar events.
2. On your iPhone go to Settings » Mail, Contacts, Calendars » Fetch New Data. Turn Off Push.
3. On your Mac, open System Preferences » MobileMe » Sync » Advanced.
4. Unregister your Mac.
5. Enable Sync again for just Contacts, Calendar and Bookmarks.
6. Go back to Advanced.
7. Select Reset Sync Data and make sure you pick Computer Overwrites MobileMe. This makes sure you’re re-uploading fresh data to MobileMe.
8. Wait until your Mac completes its sync to MobileMe.
9. Go back to your iPhone and re-enable Push.
10. Plug your iPhone into your computer and let it sync with iTunes.
11. When the sync is complete, check your iPhone: Your Contacts, Calendar events and Bookmarks should have returned!

This solution should work for both iOS 3.1 and iOS4, and on all flavors of iPhones (though I used it on my iPhone 4). Apple has a tech note available for other combinations of hardware/software, which you can read here. It’s a cautionary tale.