I've implemented the same interface as found on the eval board on an MSP430F5522
Once the button (S4 in the example above) is pressed, after about a second, my windows 7 computer shows a message stating that enumeration failed. If the USB is not connected and I press S4 and turn on the device, it is battery powered and thus skips the bootloader and goes to the main application, thus the USB must be plugged in. If I turn it on instantly after pressing the button, it works fine.
Any idea why this is happening? I feel a bit embarrassed having to tell my customers "you have to push the button and then turn it on really fast" as to why the upgrade is failing.
Thanks,
Reza