I am a Windows user and so far I've not had a single problem at all. I use USB 2.0 as the connection and it's still a fast transfer. I rip all my cd's with Windows Media Player 10 and it does just fine (although I've never use it to listen to music) *bleh* Even though iTunes tends to be the prefered choice, there's a few other programs that can be used with the iPod that are a bit more organized than iTunes. The one I've used is EphPod so you might want to look at that as well. Hope that helps.