Hello Victor,
I don´t get why defining a different transport per domain should be easier than 
defining a tls policy per domain, and my configuration is mostly automated 
anyway. The automated part becomes a challenge right now with a combination of 
dead mx plus insecure mx only - and the issue is not about automation but 
detecting the situation properly and figuring out adequate configuration.
If I get your message right, the [] are essential to match nexthop? I double 
checked and I didn´t have [] in my route so far.
Thanks, Joachim


-----Ursprüngliche Nachricht-----
Von: owner-postfix-us...@postfix.org <> Im Auftrag von Viktor Dukhovni
Gesendet: Friday, 27 May 2022 15:13
An: postfix-users@postfix.org
Betreff: Re: transport map with TLS policies?

On Fri, May 27, 2022 at 09:21:23AM +0200, Joachim Lindenberg wrote:

> I added a transport map (or “route” as mailcow-dockerized calls it) 
> that points to the alive MX

What was the exact form of the transport entry?  Presumably, something
like:

        example.com smtp:[mx1.example.com]

> plus a TLS policies for the domain and MX that asks for “may”,

As documented, the TLS policy table lookup key is the verbatim nexthop 
(including any optional ":port" suffix) from the transport table, which in the 
above case would be:

    [mx1.example.com]   may

> but flushing the queue I still got “untrusted certificate”. I 
> temporarily changed my default to may and the mail was delivered.

Most likely you did not pay attention to detail or did not read the 
docuementation, and used some ad hoc list of keys that don't include the 
correct one.

> Are TLS policies applied at all after setting a domain specific 
> transport?

Yes.  But in your case (with an overly strict default policy, requiring may 
exceptions) it would be more appropriate to define a dedicated transport for 
opportunistic unauthenticated TLS:

    # Or "dane" instead of "may" if you have a working DNSSEC resolver
    # on 127.0.0.1
    #
    maytls     unix  -       -       n       -       -       smtp
        -o smtp_tls_security_level=may

and then just set the transport to "maytls" instead of "smtp" for the multitude 
of domains for which you need to make exceptions.

> I cannot rule out that the problem is mailcow specific of course.

Of course the real problem is an unreasonable default TLS policy, that requires 
extensive work-arounds.

-- 
    Viktor.

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