> I'm also not sure it matters if a TLS session is preceded by the ten
> bytes `STARTTLS\r\n' on the wire or not.

I would say it does.

In theory, it matters because the conversation is not conformant to the
protocol otherwise; a receiver-SMTP would be entirely justified in
dropping a connection which attempts to start a TLS session without
STARTTLS, and, while I don't have specific knowledge of any (I don't
use TLS), it would surprise me if there weren't implementations that
did.  (Playing fast and loose with standards conformance is in large
part how email became the disaster it currently is; doing so more just
makes it worse.)

In practice, I would say it does because the probable failure modes
when talking to a non-TLS-ready MTA are substantially better.

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