To Geezerwolf and Angerjas: When you have done the 'send to: walkman...' thing, go to the walkman under devices. and at the bottom right hand side of the media library window should be the buttons apply and config (apply only appears when you have done the 'send to: walkman...' thing). Assuming you have sent MP3 files (no OGGs, WMAs or anything else!) they should be shown in the walkmans library... once you have done this click 'apply' button and it will pop up with a box saying something like 'tracks: 29... send to walkman?' or something like that (obviously the number of tracks changes in accordance to what you send to it)... basically click the ok or yes button and then the tracks should be sent to the walkman. Dont yank your walkman out of its usb port straight away ! on the bottom left hand side of the library should be buttons saying 'play' and 'enqueue', next to them should be a little counter [updating: 12/134] [current: 33%] wait till that has counted up all the tracks (it is actually transfering them!). when its done the counter should either stop or disappear (ive forgot!) but when that happens your safe to remove your walkman! A little long! but i hope i've been able to help.