I reorganize the playlist used for that shuffle in iTunes, before I connect the shuffle. I select the playlist in the lefthand side of iTunes display (the source list) and then make sure that the shuffle symbol in the bottom bar of iTunes at the left is not highlighted. Then in the righthand side the songs of the playlist are shown in the browser window if you set the display to be in list mode. then you can drag the songs around until you get an order you like. If it doesn't let you drag them, you have not turned off the shuffle symbol in the bottom lefthand side of your iTunes dispaly. When you are done rearranging, go over to the left hand side (the source list) and ctrl-click on that playlist name (to bring up a contextual menu) and select "Copy to Play Order" and that will make the play sequence for that list be what you arranged it to be in the browser window. Then connect your shuffle and let it refresh from that playlist. When you are done syncing, disconnect the shuffle. Turn it off, turn it on. Then when you play music with the shuffle option turned off, it will play in the order you picked when you rearranged the playlist.