[Big_al]

This keeps happening to songs on my ipod when I try to play songs while plugged into itunes, can anyone give me some insight on what is causing the problem?

[surferdude9375]

It could mean a lot of things but the most common issue is that you have manually moved that song to another place and iTunes doesn't know where to look for it. Try doing a computer search for the song to see where it walked off too.