[chaley]

IIRC this already works when using the wireless device connection. Calibre enforces its rules.

EDIT: IDRC (I Didn't Remember Correctly). Calibre does not delete news from devices.

If you are transferring news using the content server then no auto-clean actions are applied. Is this what you are asking for? Given that the feature already exists with the WD connection, I am not very much in favor of adding the options to CC to do it for CS connections. Every option increases the support load, something we really want to avoid unless the gain justifies the cost.

You might be able to get a lot of what you want with either the reading list plugin or the smart eject plugin. For the latter, you would define as search that would check for need on the device that isn't in calibre. Discloser: having never done anything like this I have no real idea if it would work.