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Been working on this for the last two days and i think i finally have it down to a science, although i can't say its not a pain...but worth it since i cannot stand seeing those generic covers on my sideloaded books.
If the book cover is 300X500 pixels or in that range, or if its too high (900x1200 or so), it just will not display on the carousel. it will display in the books list, or on the quick link tab when swiping up, but not on the carousel.
My resolution? google search book cover image, save a bigger file (900X1200 will work), open it in MS Paint and resize to 575X875 (or whatever paint automatically selects when you first type in 575 for width in pixels), and save file.
Go to Calibre, and edit the Metadata to use this new cover, and convert the file to AZW3. Make sure you are converting from MOBI, i attempted from PRC and this did not work. Then upload to the kindle. I use dropbox on both devices, so i resolve on desktop then move it to dropbox, export onto kindle with dropbox app on the kindle.
This will also help resolve the issue of your sideloaded books loading into the Docs tab instead of the Books tab. Hope this helps, drove myself batty until I resolved it and figured i would share.
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