On Thu, 14 Mar 2019, Ryan McClung via Exim-users wrote:

Unfortunately no one answered my initial question.

When trying to connect to the TLS required ports it simply times out. I
have the ports listening, the ports are not blocked by our firewall, and
yet nothing works. Any thoughts?

Can you upgrade to exim 4.92 -
IIRC there were some TLS issues with 4.91 ?

Which tls library are you using - gnutls or openssl ?
Has either side been updated to support TLS1.3
(client or server,exim or tls libraries) ?
You say this problem started when you upgraded from exim 4.72 to 4.91
- IIRC exim dropped support for openssl 1.0.1 betwen those versions.

If you answered Heiko's question
  > What is the swaks command line you use?
  > When I use
  >    swaks -tlsc -p 465 -s ssl.schlittermann.de -f '<>' -t [email protected]
  > it works as expected.
I have not seen your answer.

exim -bV might be helpful too.

Have you tried swaks from the local machine as well as a remote client ?

--
Andrew C. Aitchison                                     Cambridge, UK
                        [email protected]

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