OpenSSL implementations (OpenSSL 0.9.8 mainly which is used in Debian 8 and 
others of that era of a few years ago) can't handle a server with SNI 
certificates and fails to connect. This is older --client-- openssl versions 
which we saw remote machines on the internet connecting as.
Incorrect openssl behaviour is noted here. debian exim4 for example would fail 
to connect to the smtp server when sni was enabled among other random servers 
on the net . They were rare, but our solution was to not have sni on port 25 
anyway and run it only on port 587, where clients typically have a much faster 
upgrade cycle. For the most part servers were okay but those linked with 
problematic versions didn’t like it.
Tons of details and the particular patch here:
https://rt.openssl.org/m/ticket/history?id=3038User: guest / Pass: guest








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On Thursday, January 25, 2018, 9:43 PM, Viktor Dukhovni 
<postfix-us...@dukhovni.org> wrote:



> On Jan 25, 2018, at 9:30 PM, MK <ph...@rogers.com> wrote:
> 
> I’d request considering allowing the SNI to be enabled per port.

Each port gets its own entry in master.cf, so you will certainly
be able to enable or disable SNI support for a given TCP endpoint.

> While using it in production we found a very small number (<1%) of mail 
> servers
> sending to our server didn’t like SNI- likely ancient mail servers.

This is rather intriguing... How would they even know you had SNI?
The effect of SNI is present a certificate selected on the basis
of the supplied hostname hint.  Otherwise, everything looks exactly
the same, so it is hard to imagine how said servers "didn't like" SNI.

Perhaps your server responded to some unexpected SNI names by aborting
the TLS handshake?  Postfix won't do that.  For SNI names that don't
have a matching configuration, Postfix will respond with a default
certificate, it'll be up to the client to either accept that or not.

-- 
    Viktor.



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