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So what I've narrowed the process down to is:
1. send to kindle via calibre. I do see the thumbnail placed by calibre there
2. open kindle. cover is shown then quickly replaced by downloaded cover
3. manually place the cover into the thumbnails directory again
4. open kindle. cover is not overwritten
I tried shortening the above by sending to the kindle and then manually placing the thumbnail in the thumbnails directory (even though kindle just did that) but the thumbnail is overwritten anyways.
It seems to me like the logic is "if the cover hasn't been downloaded, download it." This would explain two things:
1. after sending the book it is considered new, so the cover gets downloaded. afterward if I replace the cover art manually, it won't overwrite it because it's "already been downloaded"
2. it explains why re-sending the book via Calibre doesn't work, because each time I re-send it it is considered to be "new" again, so it re-downloads the cover art
So the trick would be to not let the kindle think that a new book is in fact new, but I doubt that's at all possible. Alternatively, it would be to set the flag (if there is any) that represents the cover having been downloaded already, so that the kindle won't go ahead and download it. I don't imagine this is possible though.
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