Gmail delivery failure (Was: Re: The TLS connection was non-properly terminated.)

Rainer Dorsch via Exim-users <[email protected]> Wed, 22 Oct 2025 20:55:08 +0200
Newsgroups	gmane.mail.exim.user
Organization	@home
Message-ID	<1889216.b8e9qBsS6s@h370>
Am Mittwoch, 22. Oktober 2025, 09:54:51 Mitteleuropäische Sommerzeit schrieb 
Odhiambo Washington via Exim-users:
> On Wed, Oct 22, 2025 at 10:39 AM Rainer Dorsch via Exim-users <
> [email protected]> wrote:
> 
> 
> > Hello,
> >
> >
> >
> > I see the same issue, but in addition the mails seem to be dropped (at
> > least
> > don't arrive on my Google account):
> >
> >
> >
> > 2025-10-22 08:17:55 1vBSAQ-006Ylq-0V <= [email protected] H=(h370.localnet)
> > [2a02:8070:8982:4ee0:1a31:bfff:fe52:1b1c] P=esmtpsa
> > X=TLS1.3:ECDHE_X25519__RSA_PSS_RSAE_SHA256__AES_256_GCM:256 CV=no
> > A=login_saslauthd_server:rd S=1707 id=3697686.eFTFzoEnKi@h370
> > 2025-10-22 08:17:56 1vBSAQ-006Ylq-0V H=gmail-smtp-in.l.google.com
> > [2a00:1450:400c:c0b::1a] TLS error on connection (recv): The TLS
> > connection
> > was non-properly terminated.
> > 2025-10-22 08:17:56 1vBSAQ-006Ylq-0V => [email protected] R=dnslookup
> > T=remote_smtp H=gmail-smtp-in.l.google.com [2a00:1450:400c:c0b::1a] TFO
> > X=TLS1.3:ECDHE_X25519__ECDSA_SECP256R1_SHA256__AES_256_GCM:256 CV=yes
> > DN="CN=mx.google.com" K C="250 2.0.0 OK
> > ffacd0b85a97d-427f009d01csi6094497f8f.
> > 404 - gsmtp"
> > 2025-10-22 08:17:56 1vBSAQ-006Ylq-0V Completed
> >
> >
> >
> > (I annnonimized my email addresses)
> >
> >
> >
> > The entries in rejectlog are all older and I do not get any message back
> > from
> > Google.
> >
> >
> >
> > I am running 4.96 on a Debian 12 system.
> >
> >
> >
> > Does anybody else see that?
> >
> >
> >
> > Any idea or hint how to debug this is welcome.
> >
> >
> 
> 
> Since you cannot debug what happens at the Gmail end, I'd suggest you check
> your Spam folder or perhaps you have a filter that handled that email. I
> run my Exim on Debian 12 too. However, my emails to Gmail all get delivered
> despite the TLS warning.

Thank for the quick response and sharing you data point. Can you tell if you 
run 4.96-15+deb12u7 or the backport 4.98.2-1~bpo12+1 ?

I can tell that my email does not get delivered, since a copy would otherwise 
sit in the gmail inbox. I initially noticed the issue on a non-gmail.com 
address which was only hosted on gmail servers.

If you are referring to a delivery failure response email, that should be 
visible in the mainlog log file of exim, shouldn't it?

Thanks
Rainer

PS: I changed the subject, since your response suggests that the TLS 
connection topic is not the root cause of the issue.

PPS: By accident, I sent this message to your gmail address directly:

2025-10-22 20:38:07 1vBdik-006hBZ-0O <= [email protected] H=(h370.localnet) 
[2a02:8070:8982:4ee0:1a31:bfff:fe52:1b1c] P=esmtpsa 
X=TLS1.3:ECDHE_X25519__RSA_PSS_RSAE_SHA256__AES_256_GCM:256 CV=no 
A=login_saslauthd_server:rd S=
5078 id=4994740.JsnAkG3lO3@h370
2025-10-22 20:38:08 1vBdik-006hBZ-0O H=gmail-smtp-in.l.google.com 
[2a00:1450:400c:c0b::1a] TLS error on connection (recv): The TLS connection 
was non-properly terminated.
2025-10-22 20:38:08 1vBdik-006hBZ-0O => [email protected] R=dnslookup 
T=remote_smtp H=gmail-smtp-in.l.google.com [2a00:1450:400c:c0b::1a] TFO 
X=TLS1.3:ECDHE_X25519__ECDSA_SECP256R1_SHA256__AES_256_GCM:256 CV=yes 
DN="CN=mx.google.com" K C="250 2.0.0 OK 
5b1f17b1804b1-475c427f74bsi17760175e9.20 - gsmtp"
2025-10-22 20:38:08 1vBdik-006hBZ-0O Completed


I assume this also did not reach you. Correct?

> 
> -- 
> Best regards,
> Odhiambo WASHINGTON,
> Nairobi,KE
> +254 7 3200 0004/+254 7 2274 3223
>  In an Internet failure case, the #1 suspect is a constant: DNS.
> "Oh, the cruft.", egrep -v '^$|^.*#' ¯\_(ツ)_/¯ :-)
> [How to ask smart questions:
> http://www.catb.org/~esr/faqs/smart-questions.html]


-- 
Rainer Dorsch
http://bokomoko.de/


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