The auto play functionality lives at the bottom of https://github.com/woutervanwijk/Pi-MusicBox/blob/master/filechanges/opt/musicbox/startup.sh You can add another mpc command at the bottom there to enable random mode. I’d imagine it’s something along the lines of ‘mpc random on’. Might be worth putting it (and maybe also a next command) before the play command so it’s random from the start.