make sure that you are adding a playlist for the gigabeat and not on your pc. your gigabeat needs to be docked or connected via usb in order for you to add the playlist. also, your gigabeat needs to be set to use the gigabeat room software and not media player. once the gigabeat is set in and you have selected it, you should be able to go to File and add a new playlist, then select the songs you want to add to the playlist by right-clicking on them. hope this helps.