Hello,

Is there any way to force OpenSMTPD to use SMTPS on port 465 for
outgoing relays (without using a smarthost)?

I'm trying (and failing) to configure OpenSMTPD to relay outgoing mail
(v5.4.4 on OpenBSD 5.8 and also tried v5.7.3p1 on Linux). Here is my
barebones smtpd.conf:

listen on localhost
accept for local deliver to mbox
accept for any relay

I've tried many other possible configurations. Perhaps revealingly, if
I set it to forward via a smarthost I have credentials on with explicit
SMTPS:

accept for any relay via smtps://<relay>.com

then things work fine. If I don't explicity specify SMTPS then this
fails as well with similar debugging output. Network monitoring
indicates that when mail is successfully sent via smarthost, the
connection is initiated on port 465. However, with other configurations
all connection attempts are made on 25 and the destination servers
never respond. I have tried this with multiple destinations. Name
resolution succeeds in each case, but the destination servers never
respond on port 25.

I know from past experience with Exim that I must explicity tell it to
use SMTPS for outgoing relays. I suspect that I'm having the same issue
here, but I can't figure out how to configure this behavior on
OpenSMTPD. I can set 'smtps' as an option on the 'listen' control word
but not on 'relay'. Any help or suggestions would be greatly
appreciated. I can attach full debugging output if requested, but again
it seems clear from the network logs that smtpd is repeatedly trying to
connect to remote hosts on port 25 with no response, while perhaps it
should be trying on port 465.

Thanks,
Jeremy

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