stupid iPod

So last Monday at Fizz I stepped in to DJ at the last minute, and all I had was my iPod. I DJed by continually adding songs to an on-the-go playlist. It's a very handy feature that I use all the time, but it has one very irksome glitch. If you add songs to the end of a playlist while the playlist is already going, the iPod will not cycle through the whole list. Instead, it will give the appearance of cycling through the list, but actually go back and start playing the first track again. So for instance, say that I set up a playlist with four songs on it:

1. Louis Armstrong - Georgia Grind

2. Lavern Baker - Gimme a Pigfoot
3. Artie Shaw - Everything is Jumpin'
4. Duke Ellington - Peckin'

Then I hit play, and as Lavern Baker is going, I add two more songs to the list:

5. Cab Calloway - Wah De Dah
6. Jay McShann - Gone with the Blues

So after Duke Ellington finishes, the iPod gives the appearance of playing Cab Calloway. But the music coming out of the wire is actually the start of Louis Armstrong again.

Anybody else had this problem? Is there anything you can do about it?