Why are my emails getting caught in my outbox and not sending?

Why are my emails getting caught in my outbox and not sending?

This started happening to me immediately after updating to 10.9.3. None of the suggestions that I could find through Google (orotherwise) helped at all. Mail.app simply does not try to empty the outbox. I would call AppleCare, but they'll just tell me that the software is fine and that it's unreasonable for me to expect to be able to send email.
Apple support is a dim shadow of it's former self, but it correctly reflects teh state of Apple development. I picked a horrible time to switch to Mac.

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