I had the same porblem when i got my ipod. I had ripped about 30 cd's with windows media 9 and didn't want to re rip all the cd's. There is a program i used called Audio Conversion Wizard. It worked really good, but i didn't feel like purchasing it so i only used the beta. You can only convert 5 songs at a time with the trial version so it will take a while if you do it the same way i did. Hope that helps.