I have a Clip Sport and the Sleep setting works exactly as you described:
Please be informed that the “Sleep” setting on your Clip Jam player has been designed this way so that you can set it up anew in each session that you are using your player.
I own several DAP devices (iPods, iPhone, Cowan, Creative Zen) and none of them will automatically restart their internal Sleep Timer. Apple devices will remember the last selected Sleep Time but not auto-restart the timer. I wonder if any current available DAP includes an auto-restarting Sleep Timer?
