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This has been a headache for many of us and I have been on amazon support several times. It does not only happen on Kindles but the respective kindle apps as well. What I have found is that is no amount of reconverting will do the trick.
Rather, what has worked for me, after the last tech support suggested all the data was not loading, was to resend the book through the kindle email address that is assigned to me, wait till the book fully downloads, wait some more, and wait some more before opening the file. Since then, my covers have stayed, but once in awhile I have to resend from calibre. this may or may not work for you, but I was tending to rush open the book to see if the cover would remain which only resulted further my issue.
As I much as I have loved reading on kindles in the past, the software platform leaves much to be desired.
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