iPod HELP!

[Jeffros Spec V]

I have this ipod. Songs I download from Itunes load onto my ipod each time I plug it in. Thats fine.

Now, I downloaded limewire and download all these songs and when I open Itunes theres a thing under "source" that says "Jeff's Limewire Tunes" and that gets updated automatically updated once I donwload the songs but I can't get those songs to load onto my ipod unless I manually add each song onto my Library" even if I hit update ipod or anything like that.

Any suggestions?