Can't Drag Songs to Change Order??

All the playlists I've ever created on my iPod I can just drag songs up and down to change the order they play in. I just created a couple of new playlists, and they won't let me change the order of the songs. I can't drag them up and down. I tried reorganizing by using different columns. Even though it resorts on the iTunes screen, when I eject the iPod, the playlist is still in the wrong order when I try to play them.
What did I do different on this one? Why won't the playlist order change?

You do the 'rearrainging" prior to transferring the playlist to "Devices."

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