Originally Posted by birdy

Where are you having trouble...are files going to the iTunes library but not to the iPod, or are they not going to the iTunes library? Or are some files transferring, but not others?

Are you dragging & dropping, or using file > add to library? Have you tried both ways?

Do you have your iPod set for automatic or manual updates?

I'm sure you're frustrated & sometimes iTunes & iPods can be a pain. The reason that I yelled at you before was that you posted way too many times & it was a pain having to go & delete all those extra posts.