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by danmarg 3749 days ago
I don't think the use of a single port is really at the heart of the problem. Even if SMTP with TLS ran over port 26 (say), you wouldn't know if a timeout on port 26 meant the server wasn't listening on port 26 or a MITM had just chosen to drop your packets.

Discovering if someone supports Protocol++ if the fallback to Protocol is insecure is a hard problem.