FWIW, iphone does NOT sync with Outlook 2010 yet, but then, the 2010 version is still in Beta, which probably has something to do with that.
I DID have it set up to sync with the Outlook 2007 calendar function. iTunes tells me it will sync with the contacts, e-mail, etc. in outlook too. I don't remember if I did any of the other sync functions with outlook 2007.
I think that with a subscription to "Mobile Me" the iphone and your outlook stuff will keep synced all the time via the "cloud" -- I'm not sure how that works!
Karen in Boise




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