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If user has to get another Kindle (or presumably several Kindles linked to the same account) then Amazon will just send the books again along with any annotations or other files specific to that user.
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Actually it's even simpler than that. Whispersync does not synchronize "content" between devices/apps at all. It just synchronizes the
list (archive) of available Amazon purchases to each device/app, but the end user must still decide—book-by-book—which ones they want on which device/app. If they
have decided to download a book to that particular device/app, then the annotations, bookmarks, and reading positions will naturally follow. There is no process that ensures that the exact same content appears automatically on very device/app registered to the same account.