It's not surprising that any number of things can go wrong during a major operating system upgrade, especially considering the potential number of different user configurations and computers available. OS X Lion has purred along for most users (UI changes aside), but that doesn't mean one or two bugaboos can't be lurking in the big cat's furry mane.
In our case, OS X Lion was successfully installed just fine on a mid-2010 27-inch iMac Core i7 -- or so we thought. A few days later, we happened to realize that MobileMe contacts and calendar events weren't pushing to our iPhone 4 and iPad 2, even after using Lion Cache Cleaner post-install to clear out any cruft remaining from Snow Leopard.
Opening the System Preferences > MobileMe pane and heading to the Sync tab, we were shocked to find that the "Synchronize with MobileMe" box was completely unchecked! Prior to installing OS X Lion, all was functioning just fine. Time to put on the Troubleshooter Hat and get to work!
Our first troubleshooting attempt was to simply re-enable sync and get things going again with automatic sync. But the preferences pane instead threw up an error that there was already an existing computer using the same name -- as in, the same iMac previously running Mac OS X 10.6.8. Weird! No matter, we instructed the error window to deregister the iMac and set it up from scratch by clicking the Advanced button. Problem solved, right?
Well, if that were the case this wouldn't be much of a troubleshooting story, would it? After again enabling sync and choosing all of the options we wanted MobileMe to handle (in this case, all of them), we clicked Sync Now and sat back to watch the magic happen -- which it didn't. The sync appeared to start, but stalled out on the first option (Preferences), then failed completely. Repeated efforts also suffered the same fate.
Sensing that MobileMe's cloud had turned dark and sinister, we decided to go straight for the nuclear option -- as in, resetting sync services and pushing our clean iMac data back to the cloud.
To do this, hold down the Option key as you select the MobileMe sync icon in the Finder menu -- at the very bottom you'll see an option (hidden without the Option key) called "Reset Sync Services." Select it and you'll get this ominous-sounding pop-up:
This option will completely purge your system of its figurative sync memory, allowing you to start from a clean slate. Before pulling the trigger, you'll want to confirm in advance that your computer does indeed hold the latest, most accurate data, just in case something else goes awry in the process. If that's the case, click "Reset Sync History" and the deed is now done.
Next, head back to the System Preferences > MobileMe pane, click Advanced and select "Reset Sync Data."
With sync history erased, we now want to push a clean version of our iMac data to the cloud, so it's important to select the right-hand arrow indicating that MobileMe data will get replaced -- leaving the default "All Sync Info" to make sure it was a full nuclear strike.
A few apprehensive moments later, our iMac was happily pushing data up to the MobileMe cloud, once again bouncing between various data types (Bookmarks, Contacts, et al) and generally back to its usual good behavior. To confirm this, we created a new contact, iCal entry and Safari bookmark, then double-checked them on both the iPhone 4 and iPad 2, where they dutifully appeared as usual.
The moral of the story? Be sure to confirm that all your important system settings are still running after a major operating system installation or upgrade, just to be safe. Anyone else seen MobileMe sync go missing after installing OS X Lion?
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