On Wed, Jan 19, 2022 at 01:13:56PM -0500, James B. Byrne wrote:

> Jan 19 12:49:29 mx31 postfix/smtp[81175]: 14FDA745F9:
> to=<info.nafsyst...@gmail.com>, relay=none, delay=2877,
> delays=2877/0.02/0.13/0, dsn=4.4.1, status=deferred (connect to
> alt4.gmail-smtp-in.l.google.com[66.102.1.27]:25: Connection refused)

Note that this is the *last* connection attempt for this delivery,
earlier connection attempts (possibly successful with an SMTP-layer 4XX
result) may provide more information.  You need to find all relevant log
entries for this delivery.  Look for earlier messages in the log from
"postfix/smtp[81175]".

> In the deferred queue I see this:
> 
> postcat -vq 14FDA745F9

The "-v" is not useful.

> sender:

This looks like a locally-generated DSN with an empty sender.

> named_attribute: dsn_orig_rcpt=rfc822;info.nafsyst...@gmail.com
> From: mailer-dae...@harte-lyne.ca (Mail Delivery System)
> Subject: Delayed Mail (still being retried)
> To: info.nafsyst...@gmail.com
> Auto-Submitted: auto-replied

You're sending delay notices to outside recipients.  This is may not be
a good idea.  Consider disabling delay warnings in the Postfix instances
that handle inbound mail.  If inbound and outbound mail transit the same
Postfix instance (queue) then perhaps you can live without delay notices
in either direction...

> <h...@agtt.ca>: connect to mail.agtt.ca[216.8.180.31]:25: Connection refused

The original message could not be delivered to that address in a timely
manner.

> Reporting-MTA: dns; mx31.harte-lyne.ca
> X-Postfix-Queue-ID: 11ACD744F0

Above is the MTA stuck holding the message.

> regular_text: Final-Recipient: rfc822; h...@agtt.ca
> regular_text: Original-Recipient: rfc822;p...@harte-lyne.ca

The original recipient got rewritten to an external domain,
which is perhaps now no longer in service.

> regular_text: From: NAF SYSTEMS <info.nafsyst...@gmail.com>
> regular_text: Date: Wed, 19 Jan 2022 11:42:48 -0500
> regular_text: Message-ID: 
> <ca+5pruqzu7uruwqqjruat__tcpeqksd1sap7zgom7otmsmd...@mail.gmail.com>
> regular_text: Subject: Re:
> regular_text: To: impo...@harte-lyne.ca
> regular_text: Cc: p...@harte-lyne.ca
> regular_text: Content-Type: multipart/alternative; 
> boundary="00000000000018a8e005d5f21490"
> regular_text:
> regular_text: --11ACD744F0.1642611692/mx31.harte-lyne.ca--

The original message was possibly spam.  You might also
consider sending header-only DSNs, by setting:

    bounce_size_limit = 1

This will reduce the odds of remote sites rejecting the bounce based on
content.

-- 
    Viktor.

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