The reason that this bug is critical is because a user does not know an
email was not sent. The solution that is needed is for the user to know
that it has not been sent.  A workaround does not help if a user does
not know there is a problem. I raised the issue many years ago and have
kept an eye that the brief message that sending fails, before the email
is put in the sent folder, does not appear.  For me the circumstances
that originally caused it seem no longer to apply.

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https://bugs.launchpad.net/bugs/1215882

Title:
  Emails are silently discarded on 554 reply to STARTTLS

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