Unbelieveable. If you people only looked at the Stickys in the forum. You need to add the songs to your iTunes Music Library folder before you can add them to your iPod. How to do that, ignore the LW playlist that you see in your iTunes for a start. That LW playlist doesn't mean anything at all. You cannot copy those files only play them. It's only a playlist & the songs still reside in your LW downld folder. No conversions necessary. Just add them to your iTunes from your LW downld folder. How to do this properly? See How to transfer music to my iPod (& iTunes) (click on link) Sample images are non-functional for a few days due to a server problem but the explanation is still there.