I add songs to a Playlist and then randomize (physically) the order before syncing to my iPhone and Nano. I no longer see a way to do this in 11. Before asking why not use Shuffle on the iPhone...here is what I do. 1) Have a large Playlist with the music for my device(s) sorted by date played (almost all ALAC). 2) Copy 250 of the oldest last played songs to a Playlist named Random and then randomize them so they dont play in the same order as last time. 3) Copy to another Playlist named iPhone so I can fine tune (like moving same artist that are one after the other and...) then sync to my iPhone and play in that order.