Playlist sorting issue?

My songs won't match the order they are put in on itunes when a sorting choice is reversed..... why? This used to work before.
Here are the details:
If I set a playlist to sort by title, it works when it is on A at the top. But if I click title again, so that the list is now setup so that A is at the bottom, it won't sync correctly. Same thing is true with other ways of sorting the playlists. I click on Date Added so that the oldest songs added are on the top, sync, and it works/syncs correctly on my ipod, but then when i click Date Added again so that the most recently added songs are at the top, sync, and it doesn't work (oldest songs are still at top when I want the newest added ones....).

Sort it the way you want, then right-click on the playlist name and click Copy to Play Order.
tt2

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