I have a 4-year-old mini iPod that was only recently upgraded with the software that allows shuffle and some of the other functions long-since available on the other models. In my (limited) experience, the shuffle function does not allow random play. "Shuffle" simply changes the order in which the tracks play. Once shuffled, they will continue to play in the same order until shuffled again. You can shuffle both the albums and the individual tracks, but I am unimpressed. This seems to me to be one of iPod's few shortcomings, when compared with my husband's Creative Labs' Zen Jukebox.