Im having the same problem, but as the fix wasnt posted here it wasn´t much help to me.
Running OS X 10.9 TonePort KB37 GearBox 3.72 Line 6 Monkey 1.65
I first updated the TonePort to 1.08, but ever since, its been gone from that list. The flash driver is actually ver. 1.00 but after attempting an update, it´ll tell me it doesnt know.
Restarting the mac solves this, but the KB37 still wont work. And the error "Code 80007204 Hardware device failed to enter update mode" still appears whn i try to update flash.
Please help!
Screenshot of Monkey with the driver versions: