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Originally Posted by kovidgoyal
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That does not work with the Personal Documents service. Amazon post-processes the book to apply the Personal tag, and add an ASIN. Books with an ASIN must receive covers from Amazon's servers or have calibre sideload covers, since the Kindle software will not extract them.
Amazon does not process Dual MOBI for covers when sent through the Personal Documents service. Dual MOBIs will never get those covers. Old MOBIs will receive covers like any other book that comes from Amazon's servers.
Moral of the story: use calibre with your Kindle directly.