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Hm, so the "Your Kindle is rebooting" screen is shown by the framework right *before* the reboot, I guess. Hm, so in this case it's a bit hard to determine if the device powers off/on and whether it got into the USB downloader mode. The latter, as geekmaster said, can be determined by looking at the attached USB devices.
In Linux, I would look at lsusb and the kernel log - without any special drivers needed. I would then look if the Kindle appears in USB downloader mode and start byant checking if it stays in that mode. For Windows, I'm not too comfortable with similar ways, so probably it's constantly checking the device manager or similar, but I'm actually not sure. Currently my guess is on "constantly rebooting" (BTW, I would tape the Vol- key down, I think) or - as geekmaster suggested - an empty battery. So keeping it attached for a while is probably a good idea, too.
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