On Fri, Aug 22, 2014 at 07:16:39PM +0200, Christian R??ner wrote:

> Here is a log with Thunderbird:
> 
> Aug 22 19:00:47 mx0 postfix-submission/smtpd[29056]: connect from 
> static-201-106.deltasurf.de[193.239.106.201]:36755
> Aug 22 19:00:54 mx0 postfix-submission/smtpd[29056]: Trusted TLS connection 
> established from static-201-106.deltasurf.de[193.239.106.201]:36755: TLSv1.2 
> with cipher ECDHE-RSA-AES256-SHA (256/256 bits)

Postfix received a client certificate,

> Aug 22 19:00:54 mx0 postfix-submission/smtpd[29056]: 3hfps2157xzMl3J: 
> client=static-201-106.deltasurf.de[193.239.106.201]:36755, sasl_method=PLAIN, 
> sasl_username=de10...@srvint.net

But then client MUA authenticated with SASL PLAIN anyway.

> Now logs from Apple Mail:
> 
> Aug 22 19:14:10 mx0 postfix-submission/smtpd[29522]: Anonymous TLS connection 
> established from static-201-106.deltasurf.de[193.239.106.201]:40001: TLSv1 
> with cipher ECDHE-RSA-AES256-SHA (256/256 bits)

No certificate sent, so Apple Mail is not configured to employ a
TLS client certificate, and may not support that feature.

> Aug 22 19:14:10 mx0 postfix-submission/smtpd[29528]: Anonymous TLS connection 
> established from static-201-106.deltasurf.de[193.239.106.201]:47064: TLSv1 
> with cipher ECDHE-RSA-AES256-SHA (256/256 bits)

Your server SASL layer did not offer a SASL "EXTERNAL" mechanism,
and probably should not.  I don't think Postfix supports this
anyway.  IIRC you mentioned configuring Apple Mail for "EXTERNAL"
auth.  That won't work.

> As you see, Apple Mail does have a different behavior.

Yep, it does not employ client certificates, at least not as
configured.  Since the Postfix server requests a client certificate,
the issue is entirely on the client side.

> > Was the certificate actually used to authenticate mail submission?
> > Likely Thunderbird just used a username/password as it would absent
> > said certificate.  The message content was plausibly signed with
> > the certificate.  Don't confuse sender certificates in S/MIME with
> > TLS client certificates in SMTP (STARTTLS).
> 
> It uses the client certificate:

And yet the client also uses SASL auth.

> Received: from MacBook-Pro.local (static-201-106.deltasurf.de 
> [193.239.106.201])
>       (using TLSv1.2 with cipher ECDHE-RSA-AES256-SHA (256/256 bits))
>       (Client CN "Christian Roessner", Issuer "RNS-CA" (verified OK))
>       (Authenticated sender: de10...@srvint.net)
>       by mail.roessner-net.de (Postfix) with ESMTPSA id 3hfps2157xzMl3J
>       for <c...@deltaweb.de>; Fri, 22 Aug 2014 19:00:54 +0200 (CEST)

Right, both client cert and SASL.  Perhaps either is sufficient, if the
fingerprint is present in:

        relay_clientcerts = ${mapidx}/relay_clientcerts

> > TLS client and S/MIME, though I would use "extendedKeyUsage" rather
> > than "nsCertType?.
> 
> Ok, this is something, I can try.

https://www.openssl.org/docs/apps/x509v3_config.html#Extended_Key_Usage_

    extendedKeyUsage = clientAuth, emailProtection

> It's multi instance, yes. The reason is simple: I deploy mail
> systems that have separated border filter, mxin, mxout, submission
> and my server reflects the setups in multi instances. Patrick Ben
> Koetter helped me to split it into multi instances. And he also
> did a complete review of all my settings so chances are high that
> there might not be too much wrong here ;-)

The server configuration looks fine.

-- 
        Viktor.

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