I ran a test on this. I created a standard playlist and added the songs of an album, in track order. I synched the iPod and ejected it. The iPod showed the playlist and the songs in album order.

In my iTunes library, I sorted the songs by Song Name and redocked the iPod. After synching and ejecting, I checked the playlist on the iPod again and the tracks were sorted by Song Name.

I resorted by Album Name again (which also sorts the Track No field automatically) and deleted the last two tracks. I then added those two tracks in reverse order and resynched the iPod. The iPod now showed all the tracks in album sequence. When I looked at the playlist to find out why it didn't list the last two tracks in reverse, I discovered that by having sorted the tracks by Album Name, I had negated my custom sequence.

My next experiment was to create a new playlist and add the second half of the album, then the first half. This synched to the iPod as planned. When I returned to the playlist in iTunes I found, as I had expected, that I could move the tracks around to create a different sequence. One thing that I hadn't realised is that as soon as you sort a playlist, you've lost the original sequence and you can't move individual tracks around anymore.

I suspect that you created a sequence of tracks, then for some reason, you sorted them and thus you lost your sequence. You may have thought, as I did until I ran these experiments, that the original sequence was kept despite sorting, and only it would appear on the iPod. Moral of the story: create a playlist in the sequence you want, then don't touch it.

I see this all the time on my iPod and I think it is a bug!

I know that I used to be able to sort a list any way I wanted in iTunes and the iPod would reflect the sort. Now (since probably 4.0) I find that often the sort is on the correct field on the iPod, but reversed from the order of iTunes.

example: I'll have a "Just Added" smart playlist:

Date Added -> is in the last -> 1 days

Report this to Apple.