If we want to try and respect MTA-STS, when doing STARTTLS, the sender
needs to send the right information in the TLS SNI (Server Name
Inidication) extension. An MTA-STS-honoring SMTP client expects to
validate the X.509 certificate of the receiving MTA, but that MTA might
be known by a dozen names, unless the SNI is provided.

For example, if i'm trying to reach out to mail.example.biz but it
happens to also serve mail.example.com on the same address at port 25, I
definitely need to tell it which hostname i'm looking for, so that the
server can offer me the mail.example.biz certificate instead of the
mail.example.com certificate.

In some MTA implementations, such as Postfix 3.4, there is a parameter
(smtp_tls_servername), which sends the value to the remote SMTP server
in the TLS SNI extension.

However, the documentation seems to suggest that there could be problems
with this parameter:

http://www.postfix.org/postconf.5.html#smtp_tls_servername

        Some SMTP servers use the received SNI name to select an
        appropriate certificate chain to present to the client. While
        this may improve interoperability with such servers, it may
        reduce interoperability with other servers that choose to abort
        the connection when they don't have a certificate chain
        configured for the requested name. When in doubt, leave this
        parameter empty, and configure per-destination SNI as needed

Does anyone have any statistics of how frequent of an occurrence this
actually is, is it actually such a major problem that turning this on
will cause significant issues? It seems like Gmail does send SNI, likely
unconditionally, since it attempts to negotiate TLS1.3, where SNI is
expected. This suggests that it is likely safe to send SNI, but it would
be good to find out.

Those of you running MTAs, can you gather from your logs all the servers
you've connected to in the past, and attempt to connect to them with SNI
and collect those which abort connections, so we can find out what needs
to change to make this parameter safe to enable? Does anyone have any
contacts at any of the mail gamification sites that can add this check?

If we wish to respect MTA-STS, we need to get servers who are doing this
to stop doing this.

Sorry for postfix-users, who have already heard this, I wanted to reach
a wider audience.

-- 
        micah

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