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

On Wed, Oct 22, 2025 at 10:57 PM Rainer Dorsch via Exim-users <
[email protected]> wrote:

> 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 ?
>

```
wash@eu:~$ exim -bV | head -n 4
2025-10-23 12:25:57 cwd=/home/wash 2 args: exim -bV
Exim version 4.99-RC4 #2 built 19-Oct-2025 14:49:12
Copyright (c) University of Cambridge, 1995 - 2018
(c) The Exim Maintainers and contributors in ACKNOWLEDGMENTS file, 2007 -
2024
Hints DB:
wash@eu:~$ cat /etc/debian_version
12.12
wash@eu:~$ cat /etc/os-release
PRETTY_NAME="Debian GNU/Linux 12 (bookworm)"
NAME="Debian GNU/Linux"
VERSION_ID="12"
VERSION="12 (bookworm)"
VERSION_CODENAME=bookworm
ID=debian
HOME_URL="https://www.debian.org/"
SUPPORT_URL="https://www.debian.org/support"
BUG_REPORT_URL="https://bugs.debian.org/"
wash@eu:~$
```

Typical SMTP transaction with the TLS error:

```
2025-10-23 00:00:15 1vBfwN-00000007j6e-0Dls H=gmail-smtp-in.l.google.com
[173.194.69.26] TLS error on connection (recv): The TLS connection was
non-properly terminated.
2025-10-23 00:00:15 1vBfwN-00000007j6e-0Dls => [email protected] <
[email protected]> R=outbound T=remote_forwarded_smtp S=5568 H=
gmail-smtp-in.l.google.com [173.194.69.26] I=[62.169.28.150] 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
4fb4d7f45d1cf-63e3f30c564si31238a12.192 - gsmtp"
2025-10-23 00:00:15 1vBfwN-00000007j6e-0Dls Completed
```


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?
>

That's a successful delivery, as you can see code 250.

The only differences between my server and yours - yours is using IPv6
while I am using IPv4;
I am running Exim 4.99-RC4, but that doesn't matter as this TLS error
message has been there for a long time and it is non-fatal.

--
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]

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