I think you're getting confused with the LW playlist that shows in iTunes. Ignore that!!! You can't add songs to iPod using the LW playlist in iTunes. I'd also recommend updating your iPod manually. BTW how are you adding songs from limewire to iTunes? You need to either drag & drop them onto iTunes or use the add command from the iTunes file menu. The songs MUST be within the iTunes library before iPod can import them. Remember the LW playlist within iTunes is only a playlist but the actual song files are still within your LW download folder.