I have the same problem too. What works for me is, that I reboot or power cycle my iPod classic, then when it comes back, that same song plays back fine. I really like this unti (NEX 4100), but I really don't like the idea that one speads $$$ on this unit and it doesn't work that way it should. I used to have an Alpine W505, and it's iPod playback was way better, and the album art was not an issue.