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@Trevorknelson: I'm glad you posted this, as I am having the exact same issue and thought I was losing my marbles. Like you, book covers show up when I download to my iDevice, then after a few syncs, they disappear. Like you, it just started happening recently, and was never a problem before. I'm not doing anything differently on my end with Calibre, so I'm guessing it's an Amazon bug. Darndest thing!
Also, fwiw, I use mobi-both, so I don't get covers on my Voyage, but I do/did get covers on my iDevices until this weird gremlin appeared.
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