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On Tue, 2015-06-23 at 20:16 +0000, Phil Pennock wrote:
> A key issue though is that by default, Exim will fall back to
> unencrypted because encryption to MX is opportunistic.

Sendmail as a client sends EHLO, receives an offer of STARTTLS, sends
STARTTLS command and uses openssl to switch to an encrypted connection.
When openssl fails the handshake, sendmail just temp fails 403 the
attempt and requeues the mail. In particular, sendmail does not
immediately retry without STARTTLS, leading to an eventual delivery
failure - by default 5 days later.

Does Exim (immediately or delayed) retry that connection and
(temporarily or permanently) ignore the offer of STARTTLS? Does anyone
know the behavior of Postfix or other software in this circumstance?

What is the "correct" behavior in this case? The recipient is offering
an encrypted channel that we cannot (well, will not) use. If everyone
backs off and sends plain text, the recipient will never realize that
they should upgrade their DH parameters. We can easily write a script to
tail the log files and automatically add "Try_TLS:server NO" entries to
/etc/mail/access. But should we?

Given how widespread Redhat EL5/6/7 servers are, the inability of
RHEL6/7 to send mail to RHEL5 servers that have enabled TLS is
surprising.

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