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Re: Email submission.



In-reply-to: <[🔎] ZDtpl6ID+Q1TIZ+j@axis.corp>
References: <[🔎] 9f8dd61d64d9c253af0fe23b546e6de3@easthope.ca> <[🔎] ZDtpl6ID+Q1TIZ+j@axis.corp>
Subject: Re: Email submission.

    From: David Wright <deblis@lionunicorn.co.uk>
    Date: Sat, 15 Apr 2023 22:20:55 -0500
And in turn, this reply doesn't contain any feedback to my suggestion
of installing the backported exim, which claims to support tls on connect.

Yes, sorry.  Too wary of venturing beyond stable.

Now installed backported exim. Unnecessary blanks removed for legibility here.
$ dpkg -l | grep exim
ii exim4 4.96-14~bpo11+1 all metapackage to ease Exim MTA (v4) installation ii exim4-base 4.96-14~bpo11+1 amd64 support files for all Exim MTA (v4) packages ii exim4-config 4.96-14~bpo11+1 all configuration for the Exim MTA (v4) ii exim4-daemon-light 4.96-14~bpo11+1 amd64 lightweight Exim MTA (v4) daemon

No new question in "dpkg-reconfigure exim4-config".  Shouldn't it ask
to choose between STARTTLS and TLS-on-connect?

/etc/exim4/update-exim4.conf.conf is unchanged by adding the backport.

My only remaining advice is to try everything on every port.
Frequently, one particular method is advertised, but the software
may allow other protocols/methods too. For example, the SMTP
port and commands that mutt sends my posts with is quite different
from those used by my hand-crafted automated emails (same hosts).

Certainly trying many combinations. Technical support from the smarthost
also might recogize a detail I'm overlooking.

I don't recall ever seeing a debug message with a heading.

Not a heading for the file or a comment explaining one line.
Headings for more abstract levels of progress.
Eg.
"Evaluating whether delivery is local."
"Submitting password for user <me> to smarthost <there>."

Incidentally the debug text has formal syntax such as this.
08:29:51 3623 }{${if def:sender_ident {from ${quote_local_part:$sender_ident} }}${if def:sender_helo_name {(helo=$sender_helo_name)
Does anyone recognize a language?  Exim internal syntax?

I've never seen anything to be gained from comparing incoming and
outgoing email configurations.

Nothing to compare in configurations.  Just an observation that POP3
via stunnel is painless. I might try bypassing exim and sending
directly from MUA to smarthost.  Optionally through stunnel.

That seems to be moving on to newsreaders. ?

No, no.  https://wiki.debian.org/Pan has the only mention about
starting stunnel I've found in Debian documents.  Pertinent to receiving
mail here. Recklessly appended the topic rather than send another
message. =8~/

Thx,                        ... P.


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