OK, I have has this problem since the 1st gen Touch and now the 2nd gen Touch. I drag mp3s from PC to iTunes. It installs them. I highlight all tracks, right click, get info. Drag the image that's for the cover to the box. It shows there. I hit OK. It does all the ID tag stuff and done. I go to music, on album view that album is a black box..I switch to landscape where the images show and get to that album...black, no cover. I scroll past to next album....the one that was black, I can see the cover showing that it's next or I just passed it. Go back to it...black. Album cover will NOT show when that album is selected nor when a song from the album is playing. I had this working with an old version of iTunes on my gen 1, but never had it working on my gen 2 cause it requires a newer version of iTunes. Anyone able to help me...someone, please!!!