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a popup appears telling me the mail in the outbox is not ready to be sent. I have to open and press send to get the mail out.
This is a new edge case introduced by the addition of outgoing filters that I hadn't thought about. Nice going ;) The problem will be avoiding infinite loops, say when one outgoing mail generates MORE outgoing mail which spirals out of control. Hmmm maybe the replies and forwards generated by filters don't go through the normal outgoinging filters so that these sorts of issues are avoided.