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I regret to say that we have not been successful at determining the magic necessary to make upload covers work on first send.
However, we have added an option that tells calibre to upload the covers on every connect. If you are using automatic metadata management, setting this option to Yes will cause the current covers to be sent to the Sony every time you connect it to Calibre. Jackie_w has tested it, and it seems to work. Clearly this isn't as good as having it work the first time, but correcting the covers automatically at next connect is better than having to resend the book. As a bonus, if you change the cover, the new cover will be put on the device on the next connect.
The new option (in preferences -> plugins -> device plugins -> Sony) will be available in the next release.
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