With Outlok 2011's release, only contacts were supported via Address Book, and mishaps were reported when Calendars were eventually turned on: In the past, syncing other types of data than mail was accomplished by setting up MobileMe in each of the corresponding apple apps(iCal, Address Book) and then enabling SyncServices in Entourage to have it push and pull updates to the data. I understand you eventually want to get data to your iPhone, but Apple's central MobileMe service just can't talk to Outlook as you're hoping, which I will now attempt to explain: Outlook, like Entourage before it, isn't setup to support MobileMe natively as an account that it will sync more than Mail with.
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