Without doing any investigation (so finger in the air moment here) I'd guess the Zune software was passing temporary certificates from the machine to the zune. The zune security manager allows sync for the life of the certificate. Resending the same certificate would be useless as it would be expired.
Thats how I would have written it anyway. I've not looked in to hacking the zune yet as I'm a java bod, but I am tempted to start at the least sniffing the usb data and seeing whats what.
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