Finally found it :-) RCPT domain changed not long ago from Gmail to
Microsoft and uses mta-sts. Out mta-sts resolver still had the policy
for gmail, therfore the delivery to Microsoft could not be verified. We
just deleted the policy for gmail from our mta-sts resolver and now it
has the correct policy for Microsoft.

Thanks @Victor for your support

Cheers

tobi
On Mon, 2024-12-09 at 22:51 +1100, Viktor Dukhovni via Postfix-users
wrote:
> On Mon, Dec 09, 2024 at 12:03:02PM +0100, Tobi via Postfix-users
> wrote:
> 
> > > Is that preventing mail delivery, or just noise in the logs?
> > 
> > not just noise. It prevents our delivery and finally we bounce back
> > to
> > sender with "expired"
> 
> SMTP defaults to unauthenticated TLS.  What settings, if any, on your
> end cause you Postfix to care about the presented certificate
> (chain)?
> 
> > Thanks for the hint with posttls-finger. Using that I can see that
> > the
> > certificate gets validated properly.
> 
> Chroot issues with trust-anchors?
> 
> > > openssl verify -show_chain -untrusted  <(posttls-finger -cC -
> > > lverify
> > -Lsummary "leha-ch.mail.protection.outlook.com" 2>/dev/null) 
> 
> You're neglecting to call "verify" with an "-untrusted" argument to
> augment the chain with required intermediate certificates.  Did
> someone
> improve "verify" at some point to load additional certs from the
> provided file.
> 
> > depth=0: C = US, ST = Washington, L = Redmond, O = Microsoft
> > Corporation, CN = mail.protection.outlook.com (untrusted)
> > depth=1: C = US, O = DigiCert Inc, CN = DigiCert Cloud Services CA-
> > 1
> > (untrusted)
> > depth=2: C = US, O = DigiCert Inc, OU = www.digicert.com, CN =
> > DigiCert
> > Global Root CA
> > 
> > does this mean that postfix does not use SNI and therefore gets the
> > default cert which also openssl confirms that it cannot be
> > validated?
> 
> Postfix does not by default use SNI, unless DANE is enabled, but
> it does not seem to matter in this case.
> 

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