Hello Viktor,

thanks for your valuable assistance.

>Author: Viktor Dukhovni via Exim-users
>Date: 2024-07-08 04:30 +200
>To: exim-users
>Old-Topics: [exim] Re: Follow-Up: Debug TLS/DANE problems it is GnuTLS!, 
>[exim] Re: Follow-Up: Debug TLS/DANE problems it is GnuTLS!, [exim] Re: 
>Problems with outgoing DANE-TLSA, when CA-anchored test fails, [exim] no SNI 
>used, when sending TLS secured messages out
>Subject: [exim] Re: Debug TLS/DANE problems


>Perhaps the issue is as mundane as you not having a local validating
>resolver in /etc/resolv.conf, so that the destination domain looks
>unsigned to Exim? Can you post the output of:

>    $ dig +noall +stats +comment -t mx et.lindenberg.one | grep -E '^;; 
> (flags|SERVER):'

>On my system, I see:

>    $ dig +noall +stats +comment -t mx et.lindenberg.one | grep -E '^;; 
> (flags|SERVER):'
>    ;; flags: qr rd ra ad; QUERY: 1, ANSWER: 4, AUTHORITY: 0, ADDITIONAL: 1
>    ;; SERVER: 127.0.0.1#53(127.0.0.1) (UDP)
>Note the "ad" bit in the response *flags*, and "127.0.0.1" for the
>*SERVER*. I have a validating local resolver.


I checked into that already also. First I used my own nameserver, where the 
output just looks as
yours.
 dig +noall +stats +comment -t mx et.lindenberg.one | grep -E '^;; 
(flags|SERVER):'
  ;; flags: qr rd ra ad; QUERY: 1, ANSWER: 4, AUTHORITY: 0, ADDITIONAL: 1
  ;; SERVER: 127.0.0.1#53(127.0.0.1) (UDP)
But later I changed to to the nameservers from my hoster, where the output 
looks like this:
 dig +noall +stats +comment -t mx et.lindenberg.one | grep -E '^;; 
(flags|SERVER):'
  ;; flags: qr rd ra ad; QUERY: 1, ANSWER: 4, AUTHORITY: 0, ADDITIONAL: 6
  ;; SERVER: 185.12.64.1#53(185.12.64.1) (UDP)

So that can't be the cause from my knowledge point.

>Or, more likely, you're not using DANE at all, either because it is not
>enabled in your Exim configuration, or because you don't have a
>validating local resolver in /etc/resolv.conf, or it does have
>"options trust-ad" (needed on recent glic systems).

>Which then leads to no default SNI, and then to the problematic
>keyUsage.

>DANE is not actually taking place.

All I can see is, that DANE takes place (for the OpenSSL based exim), as I pass 
the test from https://blog.lindenberg.one/EmailSecurityTest

Analysis 

Mailserver (Prio)
Adresse(n)
Aussteller Rootzertifikat
DNSSEC
STARTTLS
TLS Version
Zertifikat
Passende TLSA
MTA-STS

mx.sub.myDomain.de (10)
159.69.xx.xx
ISRG Root X1
Mx, A, Tlsa
Success
1.3
Trustworthy
Ok
No Policy
?
Obligatorische Transportverschlüsselung


 
?
?
 
 
 
?
Qualifizierte Transportverschlüsselung


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?
 
 
 
?
RFC 7672 SMTP-DANE


?
?
?
 
?
 
?
RFC 8461 MTA-STS


 
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?
 
?
 
Summary


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Netzwerkinformationen









My mailserver avoided untrusted certs, but was sending to the TLSA-trusted cert.


>> I did a tcpdump on my test environment, sending mails to a couple of 
>> domains, DANE secure, without
>> DANE, but enforcing STARTTLS and such, allowing STARTTLS.
>> I did this three times, using different compiled exims for the same 
>> configuration:
>> - the distribution original exim "Exim version 4.96"
>> - my own compiled exim with OpenSSL-GNU from debian "Exim version 4.97.1"
>> - my own compiled exim with self compiled "openssl-3.3.1" "Exim version 
>> 4.97.1"
>> all connections were established without using SNI, just a plain "Client 
>> Hello" in the dump!

>> Two servers with "Exim version 4.93" are also not sending SNI in TLS.

>You really should have included the "Transport Layer Security" portion
>of the packet that includes the TLS Client Hello. But if the problem
>is at the DNS layer, this is not surprising, so perhaps not needed.

I enclose two full logs, one with the GNU-TLS Version of exim and the other 
with the OpenSSL Version



>--
>    Viktor.

Attachment: logs.tgz
Description: Binary data

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