Hi there, I dont come on the forum very often, but I also had a sony walkman for christmas and what I do is rip the cd's with windows media player then make sure you have the walkman plugged into the usb cable you then select the sync option at the top of the windows media player page. It then usually takes you to your library. This is where you need to take care and not sync everything that you have on your computer to the device. So what you do is highlight the items you want on the player then drag them to the right hand side of the screen which is where you walkman details are. Once there you say start sync and that should do it. It tells you when you can disconnect your device. Hope that helps. Lisa