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Actually, this reminds me about something I was going to suggest as a tweak to Calibre's job queue. Specifically, can the queue be made pausable and unpausable?
From the gui perspective, just a button next to the queue which is play/pause to control it. When paused, the queue would, erm, pause. And not restart until it's unpaused *even if you add more jobs to the queue*.
Then each job can check whether it's doable or not when it attempts to execute.
This would let me, for example, queue books individually to be sent to the device without them being sent the instant i add them to the queue. Calibre could then, when the queue is restarted, send them all in one batch (or in a sequence of individual jobs - doesn't really matter which from a user perspective).
This would also solve the OP's problem as a nice side-effect.
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