Greetings!
There have been issues with timing the serial port under windows 2000. Basically, in many cases the upgrader does not see / find the empeg. This is more an issue with windows 2000 - the upgrade program cannot get to the serial port fast enough to get into the upgrade mode. (You will notice in booting with hyperterminal that there is a short moment where you can abort the player run and enter the upgrade mode - this is not responded to quickly enough under W2K.)
Best solution I have found, fun the upgrade utility, let it get around half way through the discovery phase and then plug in the empeg. This way, the upgrade utility already has the serial port and is in loop watching for it. Other fixes that have helped: verify that there are no drivers (Palm, tablet, etc.) running off the serial port, disconnect the ethernet and USB ports during an upgrade.
Paul G.
SN# 090000587 (40GB Green)
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Paul Grzelak
200GB with 48MB RAM, Illuminated Buttons and Digital Outputs