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It seems fairly clear that the kindle firmware tries to update covers for "newly" uploaded books, exactly once. Before the change to amazon's servers, the firmware would do it, and fail and keep the calibre generated thumbnail. After the update, it does it and replaces the thumbnail with its spurious "no cover available" image.
So this will affect any book that the firmware thinks is "newly added" on a date after the amazon server was changed.
Assuming amazon refuses to fix their firmware/servers to do the sensible thing, the best possible workaround seems to be for calibre to restore changed thumbnails on subsequent reconnects. This means to send a book to the kindle, with cover, you have to send, disconnect, wait for the Kindle to destroy the cover, then re-connect and have calibre restore the cover.
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