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Had a similar issue with covers when used Kindle Previewer 3 to generate MOBI from ePub and then Calibre's plugin to extract AZW3. After sending that file to Kindle cover never showed up regardless is device in airplane mode or not.
When tried to convert ePub to AZW3 in Calibre directly - all was good on my kindle and cover was there even after it was synced over wifi.
Interesting that in Kindle Previewer the first page of each book has a cover image.
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