iPod skipping songs?! HELP!

Quite querulous... What format of song is it? I had a few MP3 that did the same thing, so I converted them through the Advanced menu and now they're fine. Notably, I converted them to the same format and bitrate that they already were, as anything else would have seen a larger drop in quality. You can change these conversion settings in the iTunes Preferences, under Importing. Converting the song creates a new version, and this new version played properly for me. I then deleted the old version.

 

A purchased song? This seems to be happening a lot since the last update. My Nano started doing it too the other day.

If it is a purchased song, try unchecking it in the iTunes playlist, syncing the iPod so that it's not on it any longer. Then log back out of and into your iTunes account, recheck the song and resync the iPod. If that' doesn't do it, then you might have to restore the iPod.

 

Had the same thing happen to a iPod mini. (And they weren't even purchased songs - just songs ripped from a CD). After trying a few things and restoring the iPod to no avail, I took it into the Geniuses at my Apple Store and got a new one.