Well, after looking at the DROID user manual, the only thing it mentions in regards to Outlook sync is web based Exchange sync (manual pg. 20). I would guess that means it won't sink with Outlook via USB out of the box. Previous versions of Android did not sync w/Outlook out of the box either. Most people either used an app to sync outlook -> google or did other weird workarounds.

However, there very well could be an app that allows direct Outlook sync via USB. Not sure, but I know I've never seen one.

Jason Bottjen