On Sat 17 May 2025 at 15:11:14 (-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?

My observations would be:
1 What are localhost, mail.easthope.ca and easthope.ca?
2 What does "configured according to https://wiki.debian.org/Exim"; mean?
3 Swaks should have given you a blow-by-blow account of each submission.
4 Exim applies an address retry timeout, rather than continuously
  knocking on an unanswered door.

On Tue 27 May 2025 at 07:23:36 (-0700), pe...@easthope.ca wrote:
> Similarly, I've used the Oberon Mail module for several years.  It
> submits messages to the smarthost through stunnel with no intervening
> MTA.  Oberon Mail and stunnel are straightforward to configure.

Similarly, I use mutt to send my emails directly to my email
provider's smarthost (no tunnel). I like the instantaneous feedback
on the submission process. Using an MTA can result in snags not being
reported straightaway, as it merely queues it for retrying later.

I configure Exim to handle all intra-LAN emails, which I don't need
to compose with an MUA: they're typically system-generated. Most are
sent to one particular host, but using an MTA has the advantage of
queueing them when any destination host is switched off.

Currently, I use Swaks to send a daily email to a hotmail account,
allowing me to determine my home IP address from wherever I am.

> On Tue 27 May 2025 at 14:20:14 (+0530), didar wrote:
> > 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!
> 
> Good.  Thanks.  I reviewed exim4 more for interest than necessity.
> When there is time, can follow up on your suggestions.

I'm not sure it's worth trying to configure Exim without having
a clear picture of what you want it to do with it, and how it
will fit into your overall email strategy. (Obviously I'm talking
about going beyond sole use of   dpkg-reconfigure exim4-config
in a LAN with a single PC.)

Cheers,
David.

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