shuffled playlists

I'm sure this has been explored, but I can't seem to find "the" answer...

I'm using the most current version of iTunes on Windows 7. In previous versions of the program, clicking on the shuffle icon randomized a playlist. Then, when syncing with an i-device, the playlist's random order was also synced. Now, the shuffle icon simply plays the tracks in a random order.

How can I sync the random order to my device?