Maybe you should wait to load the 1.0.2 software on your iPod Classic...Updated iPod Classic 160G to 1.0.2... can add videos, photos but when I add any music/ music vids it goes into a reboot loop.Note: we (Apple Product Specialist) tried loading a song from iTunes store by its self... worked fine.Also, When I received iPod it was running fine on 1.0 S/W with all music files loaded... Did apple put a bug in S/W to push users to purchase songs from iTunes... others are having this prob.