On Sat, May 17, 2025 at 03:11:14PM -0700, pe...@easthope.ca wrote:
> /etc/stunnel/stunnel.conf has 
> [smtp]
> client = yes
> accept = localhost:106
> connect = mail.easthope.ca:465
> 
> Then
> swaks -s localhost -p 106 -f pe...@easthope.ca -t pe...@easthope.ca
> sends a test message.
> 
> Whereas exim is configured according to https://wiki.debian.org/Exim
> and
> swaks -s localhost -p 25 -f pe...@easthope.ca -t pe...@easthope.ca
> produces no message and this in /var/log/exim4/mainlog.
> 
> 2025-05-17 11:54:42 1uGMgE-0004Aw-2M <= pe...@easthope.ca H=localhost 
> (imager.invalid) [::1] P=esmtp S=474 id=20250517115442.016053@imager.invalid
> 2025-05-17 11:54:42 1uGMgE-0004Aw-2M ** pe...@easthope.ca R=smarthost 
> T=remote_smtp_smarthost: all hosts for 'easthope.ca' have been failing for a 
> long time (and retry time not reached)
> 2025-05-17 11:54:43 1uGMgE-0004B1-37 <= <> R=1uGMgE-0004Aw-2M U=Debian-exim 
> P=local S=1785
> 2025-05-17 11:54:43 1uGMgE-0004Aw-2M Completed
> 2025-05-17 11:54:43 1uGMgE-0004B1-37 ** pe...@easthope.ca R=smarthost 
> T=remote_smtp_smarthost: all hosts for 'easthope.ca' have been failing for a 
> long time (and retry time not reached)
> 2025-05-17 11:54:43 1uGMgE-0004B1-37 Frozen (delivery error message)
> 
> Anything obvious?

Maybe your localhost exim instance is tring to connect to port 25 on easthope.ca
and easthope.ca listens only on port 465 and not port 25. You will have to look
into the "remote_smtp_smarthost" transport definition - the "T" in
"T=remote_smtp_smarthost" means the transport that exim is trying to use,
"R=smarthost" means the router is smarthost. These terms have special meanings
under exim.

If you simply want to forward emails via smarthost, you should consider a
simpler mail agent like `msmtp'. I personally use `dma' (DragonFly Mail Agent)
for this purpose. Both are available in Debian along with some other such 
agents.

Exim is a very flexible and powerful full-fledged MTA (mail transport agent) and
is generally an overkill for this purpose. But, if you want to learn Exim then I
found it better to use the "roll your own hand crafted single conf file" in
/etc/exim/exim4.conf.

I used https://www.exim.org/docs.html this to learn how to make exim do the
things that I wanted it to. But, it took me 2 months _during the COVID
lockdowns_ to get stuff working - I am a little dull!

HTH

> 
> Thx,                        ... P.
> 
> -- 
> VoIP:   +1 604 670 0140
> work: en.wikibooks.org/wiki/User:PeterEasthope
> 

-- 
Regards,
Didar

If only Dionysus were alive!  Where would he eat?
                -- Woody Allen

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