Hi - welcome to the forums The CD that came with the player should have come with SonicStage (which is used for transferring music) and a nifty program called Image Converter (used for converting/transferring videos or photos). The process is very simple, simply install Image Converter, connect the Walkman and add the file to the list and click transfer - everything should be simple and straightforward I can't really tell you what sites you should be looking at for video downloads as that's actually illegal, but believe me, it is hard to find a SITE where you can download videos from for free For videos to convert, I would recommend sticking to videos such as AVI, MP4 Hope that answers your questions, Kwiksta