How to Solve All Your MobileMe Sync Problems

Posted 11/01/2010 at 11:27am | by J.R. Bookwalter

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Apple’s MobileMe is a great solution for Mac users with an iPhone, iPad or iPod touch (particularly if you own more than one of them), dutifully keeping your contacts, calendars and other data synced across computers and mobile devices -- that is, until something goes horribly awry, and then it can be a nightmare worthy of Halloween legends. Here are some tips for getting such problems solved -- without length tech support calls.

If your computer or device is giving you the MobileMe blues, fear not: MacLife.com is here to help! For all of its simplicity, Apple’s syncing service has plenty of hidden ways to get your data working the way it should again, from the simple to the more extreme.

How Do I Know There’s a Problem?

In addition to its push e-mail, iDisk storage and other skills, MobileMe keeps up to ten types of data synced between all of your computers and devices: Bookmarks, Calendars, Contacts, Dashboard Widgets, Dock Items, Keychains, Mail Accounts, Mail Rules, Signatures and Smart Mailboxes, Notes and Preferences.

Of the ten options above, Calendars and Contacts tend to be the most problematic, primarily because they are the most frequently updated between devices and most prone to hidden data corruption. These problems can manifest themselves with changes that don’t push to one or more devices, missing Address Book contacts and images or even worse, a bad sync that duplicates your data.

Before you proceed with our troubleshooting guidance, the first thing to check should always be Apple’s MobileMe support page. In the upper right-hand corner, you’ll find a System Status and System History which shows if the service is experiencing any outages or issues that might be directly impacting a problem you’re having. If both options show a green dot next to them, then everything is good on Apple’s end and it’s time for a few basic troubleshooting steps we recommend before you go purging or altering your data.

All Systems Go?

The first thing you should do is log in to Me.com and check your Calendar and Contacts data there -- after all, it’s directly from Apple’s cloud server, so if everything looks groovy, you likely have an issue with your computer or device. On that same note, it’s also important to make sure that all of your computers and devices are running the latest software -- for Mac OS X, hit Software Update under the Apple menu, or plug your iOS device into iTunes and click “Check for Update” to make sure you’re on the latest version.

To make sure that you’re seeing all of your contacts or calendars, tap the button in the upper left corner of Contacts and/or Calendars on your iOS device.

Last but not least, we recommend checking to make sure that MobileMe is otherwise working correctly on your device. Are you getting push e-mail properly? Have you configured your MobileMe account with the correct account name and password? These may sound like really basic things to look for, but you’d be surprised how frequently they could trip up many users.

You Backed Up First, Right?

Before venturing into the jungles of MobileMe data syncing with machete at the ready, you’ll want to make sure you have your precious data backed up in case something goes horribly awry. Even if you’re using Time Machine or some other software to keep an incremental backup of your computer’s data, we recommend archiving your Address Book or iCal in particular so you can easily import it back if you need to go back to the way things were.



From either the Address Book or iCal program, go to the File menu and select Export, choosing Address Book Archive for your contacts or iCal Archive for your calendars. You’ll be asked where you want to save these files -- we recommend an external drive, preferably somewhere different from your main backup. These files aren’t big -- we backed up nearly 1,000 Address Book contacts in less than 30MB, and a fair amount of multi-year iCal calendars in a mere 7MB, so a removable flash drive is a good place to store backups such as these.

iSync, Therefore I Am

If you’re new to the Mac or your first smartphone was an iPhone, you probably have no idea there’s a program in your Applications folder called iSync. In the dark days before iOS, Apple’s iSync was the conduit between your Address Book contacts and iCal calendar data and cell phones via Bluetooth or USB, including support for Palm OS organizers and compatible smartphones. That functionality in iSync was removed with Mac OS X Snow Leopard 10.6 last year, requiring devices such as Blackberry or Windows Mobile to rely on third-party software solutions.

However, iSync is still tied closely to the Mac OS X Sync Services -- even though you may never need to run the application, it’s responsible for the setup, configuration and synchronization between iOS devices and the Mac. That includes resetting your sync history, our next troubleshooting step which often gets things flowing again from MobileMe. (This can also be done via Terminal, but iSync is much more user-friendly.)

Browse to your Mac’s Application folder and double-click to open iSync -- disregard the small horizontal window which opens and go to menu and select iSync > Preferences. There you’ll find three sections: General, Protect your data on this computer and Advanced, the latter of which is where you’ll find Reset Sync History.

Click the Reset Sync History button and you’ll get a warning asking, “Are you sure you want to reset this computer’s sync history?” This option doesn’t actually delete your data, but instead removes a Mac OS X synchronization database and returns it to the default setting. Click the button, quit out of iSync and then do a new MobileMe data sync and check to see if things have improved.

By the way, when you first open iSync Preferences, you might see both the “Enable syncing on this computer” and Reset Sync History options grayed out -- that means the computer is doing a sync somewhere, so make sure your System Preferences are closed or wait for a background process to finish before you can proceed.



Ready, Set, Reset Sync Data!

If iSync doesn’t cure what ails you, a trip to the MobileMe preference pane -- found in under System Preferences -- is our next stop. Click on the Sync tab and you’ll see a list of the ten data types -- in the lower right-hand corner is an Advanced button, which you’ll want to click next. Now you’ll be presented with a list of all Mac or Windows computers currently tied to your MobileMe account and with just a click you can deregister any or all of them. However, the real troubleshooting magic can be found in the lower left corner, with the Reset Sync Data button.



Clicking Reset Sync Data brings you the option of removing sync data from either your current computer or MobileMe’s servers and then replacing it with a fresh copy. It’s not an all or nothing proposition, since you can selectively replace sync data for any one of the data types you’re using -- for instance, we’ll focus on Contacts, which often tend to be the most troublesome.

After choosing which kind of data you want to replace, you now have to decide where your good data resides so you can get rid of the bad stuff. Generally, data that is on your computer will be the most pure and up-to-date, particularly since that’s where most of us started in the first place, long before MobileMe was a gleam in Steve Jobs’ eye.



To replace MobileMe data with computer data: Select the left-facing arrow and then the Replace button to purge and replace what’s on your system with the data Apple has up in the cloud.



To replace computer data with MobileMe data: Select the right-facing arrow and then the Replace button, which will wipe the MobileMe server data and replace it with what’s on your computer. We don’t recommend doing this without a safe archive backup first!

Avoid using Reset Sync Data on all of your information -- for example, if your Contacts are fine but your Calendars are giving you a headache, stick to using this option on the affected Calendars. Resetting all of your sync data should be reserved only for those times when (God forbid) nothing is working and you want to effectively start over again.



Purging iOS Sync Data

Should you reset all the relevant sync data from your computer or MobileMe and find that you’re still having drama, the problem could be what’s on your iOS device. It’s time to strap on the bandana and get all Rambo on the problem.

From your iOS device(s), tap on Settings > Mail, Contacts, Calendars and then your MobileMe account. From here, you have the option to turn off Mail, Contacts, Calendars or Bookmarks -- once you do so, your iOS device will give you the option to either keep or remove your data. As long as you have good data on your computer or MobileMe’s servers, there’s no harm in purging the data from your iOS device. In fact, this step alone may even clear up your problem once you’ve turned the data type back on and MobileMe sends it down from the cloud again. (Don’t be alarmed, it may take a few minutes before that happens.)

Deleting sync data from your iOS device actually goes hand-in-hand with resetting data on the computer. After you’ve turned off a particular data type on your iOS device, tap the option to remove said data and then do a Reset Sync Data on the computer, pushing what’s good at that location back up to the MobileMe cloud. After the activity spinner in the status bar or MobileMe preferences Sync tab has stopped, turn the data type back on from your iOS device. Sit tight and let the data sync when it’s good and ready or you can get things started by going to Contacts or Calendars and watching the data repopulate -- hopefully this time without incident.

Calling Dr. Strangelove

There’s one last method for getting a handle on MobileMe bugaboos, but it’s not for the faint of heart -- in fact, one of the MacLife editors referred to it as “the nuclear option,” which Apple detailed in a lengthy support document this month for “advanced troubleshooting” with contact and calendar syncing.

Apple offers this issue only for users whose sync issues don’t involve Mobile Me in the first place (doesn’t apply to us), if you’ve reset your Mobile sync data via the MobileMe preference pane (check!) or you’ve already performed a reset sync history via iSync (double check!).

Be forewarned: You’ll want to reserve the so-called “nuclear option” only for the most dire of circumstances. While safely archiving your data (and exporting contacts from your Address Book as vCards) is part of the equation, you’ll lose (and have to recreate) Address Book Groups, which could be a real bummer for folks like us who have a lot of them in use for business. But where nothing else works, this solution has proven to do the trick.



Apple’s support document on the subject is quite extensive (a whopping 24 steps for Address Book and 11 for iCal), so we won’t repeat all of that information here, but the basic procedure involves archiving your data, using iSync to turn off syncing on your computer and deleting Application Support files, preference files and caches before heading back to iSync for a sync history reset and finally, reenabling sync on your computer.

As we mentioned, Apple’s instructions are fairly extreme where the Address Book is concerned: You’ll have to delete all of your contacts and groups, then drag the vCard you exported in Step Five back into Address Book and essentially start fresh. But before you take that drastic step, here’s another option you should try first.

Follow the first 19 (?!) steps in Apple’s support document, but instead of dragging your exported vCard back into Address Book in Step 20, try importing your Address Book Archive first. This step won’t help if you’ve got a gremlin hiding within your contacts (you’ll need the vCard option for that), but it will restore not only your contacts but your groups as well. Since your cache files got nuked in Step 16, Address Book will have to rebuild them from the newly-imported data, and that should clear up any problems (it did for an issue we had involving several stubborn contacts that refused to keep their images saved on our iPhone 4).



Either way, before you attempt syncing your imported contacts back to MobileMe, we’d defer you back to our earlier instructions on turning off Contacts on your iOS device(s) and deleting potentially corrupted data from there first. We’d also suggest a Reset Sync Data, pushing the freshly imported data back to the cloud.

Finally, check the results in Me.com’s Contacts (or Calendar) and if everything looks fine, turn the afflicted functions back on from your iOS devices and let them pull the fresh data back down from MobileMe. We’ve seen oddities involving duplicate contacts or calendar entries when we didn’t do this, so it’s better to be safe than sorry.



The Sync is Alright

In very rare cases, even all of the above might fail to bring peace to your MobileMe sync experience, in which case there could be something more sinister afoot. Contact AppleCare for support in those cases, or following yet another support document to nuke your Sync Services folder -- something they (and we) strongly discourage.

We’ve seen errant contacts or calendar events cause all kinds of random mayhem over the years, but generally reimporting this data will cure such ills. The previous tips and solutions have done wonders for a variety of sync issues as they crop up, and we’re confident that by this point, yours will be resolved as well.

Now that you’ve mastered the ninja of MobileMe, don’t forget to create a new archive backup of your contacts and/or calendars the same way we detailed earlier in this article. It’s a good idea to keep the old backup around, just in case an issue crops up later on related to all of this purging and resetting. When you’re all done, you’ll have successfully traversed the sometimes hazardous MobileMe waters and get back to syncing like a pro!

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