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That might be kind of a neat feature. Although, I have to confess, not neat enough to convince me to dive into Calibre's source code.
Shouldn't this be relatively easily implemented when one just queues the appropriate job to be activated once a device is connected (and its book list read)? The only issue I see would be carrying that job list over across a restart of Calibre, I don't know if that's possible or done already.
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