What I'd do is check to see what you have as your default Media Player. What I do is have Windows Media Player as my default player. When I download music, I have my downloads targeted into my LimeWire Shared Folder. I then cut these songs and place them in a folder that I named Music. I then select which songs that I want to be played on iTunes by right clicking on that song and go to Open With tab. I select iTunes player, and it will then be played on iTunes. You then add the songs to a playlist in iTunes. You will have no problem adding them to you iPod. I've never had any problems occur. Good Luck !!!