I have an iPod Shuffle (3rd Gen) and I know to turn on the shuffle with the play in order setting, not shuffle. I believe my problem is related to ordering the songs in my playlist and copying the music to the shuffle. First, when I create a playlist and order the songs, does sorting affect the outcome of my play order? How does it know what order to use in the first place? In my opinion neither sorting nor which song was copied into the list first should matter. When you have your songs in order, you should simply be able to select "Copy to Play Order" and iTunes should lock in the playlist order you have set visibly on the screen. This, however, doesn't seem to happen. My shuffle still plays songs in Alphabetical order by Artist. Why?? I have no idea. Why did it choose Artist? Why not Alphabetical by Song name? I don't want that either, but if I understood why it is choosing to sort alphabetical by artist, I might get a better understanding of why it doesn't work right for me. Can anyone give me a step by step, foolproof way of getting my songs to play in order on my shuffle? Please don't leave out even the most minor step as I cannot seem to get this to work after reading many posts throughout the internet on how to do this.