Not that simple with current implementation. The Image upload is async, this means we trigger the upload and when the upload is done we get some notification about it. If we would just trigger it from CLI, it would start the upload and close before we got feedback, which means we need a sync upload function for the uploader. As always, doable but requires some effort so we can't implement it quickly.

@niksfirefly ksnip supports now custom actions where you can define exactly that behavior together with hotkeys. Does that resolve your issue?

This is now supported.