Sync over USB seems not possible currently... BUT: Sync with local Outlook items works over Bluetooth! At least under Windows 7. You pair the both devices and let Windows run through all the setup stuff. Then you open you N9 device in the "Devices and Printers" and then the Bluetooth page for the pairing comes up. There you can select to sync your items. EDIT: @jalyst I think this is one of the tips that should definitely be in the OP!