As far as the player not connecting, mine eventually just fixed itself after several synch attempts (on the USB cable). Maybe you just need to wipe the thing and start over with a fresh database?

I don't consider wiping the unit to be a useful way of solving upload/download problems in general and definitely not in this case.

The problem in this particular case is due to failure of the communication between the PC and the empeg-car over the serial cable. Sometimes a request is being sent eight or more times before the unit understands it. There is a maximum retry count of sixteen after which emplode gives up.

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Mike Crowe
I may not be speaking on behalf of empeg above :-)