Had to restore and reload firmware to my Oak. Failed many times while powered through USB (although I have successfully updated using USB power before). Decided to power through VIN using a 5V 750mA wall wart. Worked first time.

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Don't know if this was the reason I finally got it to load but it's worth trying if you are continuously failing. BTW, it's an old wall wart that I cut the connector off and soldered
some pins onto so that I could insert them into the headers or breadboards. 5V and GND wires are clearly marked so I don't reverse polarity.
Worth a try if you have you been struggling to update firmware. Be interested in knowing if this will work for others.