A. Schulze:
> 
> 
> Am 17.02.19 um 15:24 schrieb Wietse Venema:
> > A. Schulze:
> >> Hello,
> >>
> >> I updated to postfix 3.4.0-RC2 and enabled "smtp_tls_connection_reuse"
> >> Now I notice delivery problems to "gervers.com". DANE setup looks OK. 
> >> https://dane.sys4.de/smtp/gervers.com
> >>
> >> "posttls-finger gervers.com" also show
> >> posttls-finger: Verified TLS connection established to 
> >> sys1.mmini.de[2a01:4f8:162:32ac::2]:25: TLSv1.2 with cipher 
> >> ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits)
> >>
> >> But a message to the domain is not delivered. Instead I found this logged 
> >> by tlsproxy:
> >>
> >> Feb 17 14:18:28 mail postfix/tlsproxy[14593]: 
> >> sys1.mmini.de[5.9.100.168]:25: re-using session with untrusted 
> >> certificate, look for details earlier in the log
> >> Feb 17 14:18:28 mail postfix/tlsproxy[14593]: Untrusted TLS connection 
> >> established to sys1.mmini.de[5.9.100.168]:25: TLSv1.2 with cipher 
> >> ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits)
> >>
> >> But I did not found anything special "earlier in the log" ...
> > 
> > Surely the SMTP client logged SOMETHING?
> > 
> > Surely the tlsproxy daemon logged SOMETHING when it created the TLS 
> > connection?
> 
> Hello Wietse,
> 
> thanks for asking :-) Yes, of corse, there are other loglines...
> Here are the all message and connection related entries (I found):
> 
> Feb 17 10:27:54 mail postfix/smtpd[9445]: 442M9Q3L8Kzkn: 
> client=localhost[127.0.0.1]
> Feb 17 10:27:54 mail postfix/cleanup[9442]: 442M9Q3L8Kzkn: message-id=<....>
> Feb 17 10:27:54 mail opendkim[19651]: 442M9Q3L8Kzkn: DKIM-Signature field 
> added
> Feb 17 10:27:54 mail postfix/qmgr[29788]: 442M9Q3L8Kzkn: from=<...>, 
> size=1802, nrcpt=1 (queue active)
> Feb 17 10:27:55 mail postfix/tlsproxy[9450]: CONNECT to [5.9.100.168]:25
> Feb 17 10:27:55 mail postfix/tlsproxy[9450]: CA certificate verification 
> failed for sys1.mmini.de[5.9.100.168]:25: num=28:certificate rejected
> Feb 17 10:27:55 mail postfix/tlsproxy[9450]: Untrusted TLS connection 
> established to sys1.mmini.de[5.9.100.168]:25: TLSv1.2 with cipher 
> ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits)
> Feb 17 10:27:55 mail postfix/smtp[9452]: Untrusted TLS connection established 
> to sys1.mmini.de[5.9.100.168]:25: TLSv1.2 with cipher 
> ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits)
> Feb 17 10:27:55 mail postfix/smtp[9452]: 442M9Q3L8Kzkn: Server certificate 
> not trusted
> Feb 17 10:27:55 mail postfix/tlsproxy[9450]: DISCONNECT [5.9.100.168]:25
> Feb 17 10:27:56 mail postfix/tlsproxy[9450]: CONNECT to 
> [2a01:4f8:162:32ac::2]:25
> Feb 17 10:27:56 mail postfix/tlsproxy[9450]: CA certificate verification 
> failed for sys1.mmini.de[2a01:4f8:162:32ac::2]:25: num=28:certificate rejected
> Feb 17 10:27:56 mail postfix/tlsproxy[9450]: Untrusted TLS connection 
> established to sys1.mmini.de[2a01:4f8:162:32ac::2]:25: TLSv1.2 with cipher 
> ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits)
> Feb 17 10:27:56 mail postfix/smtp[9452]: Untrusted TLS connection established 
> to sys1.mmini.de[2a01:4f8:162:32ac::2]:25: TLSv1.2 with cipher 
> ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits)
> Feb 17 10:27:56 mail postfix/smtp[9452]: 442M9Q3L8Kzkn: to=<***@gervers.com>, 
> relay=sys1.mmini.de[2a01:4f8:162:32ac::2]:25, delay=1.6, 
> delays=0.11/0.02/1.5/0, dsn=4.7.5, status=deferred (Server certificate not 
> trusted)
> Feb 17 10:27:56 mail postfix/tlsproxy[9450]: DISCONNECT 
> [2a01:4f8:162:32ac::2]:25
> 
> the same tlsproxy process handled 5 other connections before this one. All 
> logged as 'Untrusted TLS connection established to'

How do those 'other' connections differ from what is shown above?

What I see is an SMTP client deferring delivery with a NEW TLS
connection. That is different from your earlier report about a
REUSED connection.

Can you confirm that the SMTP client will not deliver to this
destination with NEW and REUSED tlsproxy connections?

The error message suggests a problem in the certificate trust chain,
like an unknown root certificate. What is the output from:

postconf -F smtp/unix/chroot tlsproxy/unix/chroot

        Wietse

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