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Note: By default when sending the book to the device, metadata and covers are updated in the sent copy anyway.
And if you are referring to Cover View in the books listing on your Kindle, then the Kindle uses a saved thumbnail regardless. calibre will sideload the thumbnail (this works for MOBI too!) if the book is not a Personal Document. When resending the book that thumbnail gets updated. If the book is a PDOC I don't believe the Kindle will update the thumbnail itself.
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