i've been expieriencing problems with my ipod and itunes. for some reason it won't let me bring certain songs over from my windows media playlist or my cds, says that they are not valid files even though i bought them from the store they aren't bootleg or anything like that, the same happens when i try to put photos that i took with my digital camera. actually it won't let me put any photos on my ipod. can anybody help me? You have to convert files to ipod files. Ipod has a proprietary file type. There are a couple of different "rippers" you can use to do this kind of file conversion. Here's a link with conversion software: http://www.acidfiles.com/soft/video-conv... | 