My Outlook Contacts synced to my iPod once (after finally finding out how to so that). Since then it has never synced with Contacts again. It syncs the music just fine. Some instructions I have read mention an "Info Tab" after selecting the device. I have not seen this info tab. So I can't even get past the second step to sync Contacts to my iPod. I have updated the iTunes application once since that time. The screen view was noticeably different after that. A left sidebar was no longer there. Perhaps some of the necessary things to select for syncing Contacts are now hidden.
iPod touch, Windows
7, Contacts won't sync to iPod