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I'm having the same problem with the new Paperwhite. My old Paperwhite (and other old Kindles) never had this problem. With the new one, though, my iMac will only recognize it the first time. After that, I have to reboot the Kindle to connect again. I tested this just now against the old Paperwhite using the same cable and port. The old one works; the new one doesn't.
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