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Funnily enough, it seems the majority of the blame lies on the user trying to shoehorn a trifecta of vendors into a single overly-complex solution. Using 3 different vendors (Apple, Google, MS) for contact/calendar/email sync should have been a red flag from the beginning.

Even with 2 vendors (Apple, Google) everything would have likely gone fine if the user had just used OS X Mail and Address Book instead of Outlook. And of course, switching to iCloud (a simple 1-vendor solution) solved the issue entirely.