On Sun, Jan 09, 2022 at 10:22:36PM +0100, Joachim Lindenberg wrote:

> I configured my Email server (actually a mailcow-dockerized which in
> turn uses postfix) to enforce TLS for outbound mail. Obviously that
> will fail occasionally, but I also have a daemon watching the postfix
> queue and alerting me. Kind of works for me. Ok, while subscribing to
> this mailing list I had to add two more exceptions, because this
> mailing list uses an untrusted certificate
> (https://www.checktls.com/TestReceiver?LEVEL=DETAIL
> <https://www.checktls.com/TestReceiver?LEVEL=DETAIL&amp;EMAIL=majord...@postfix.org>
> &amp;EMAIL=majord...@postfix.org). Aren´t letsencrypt certs cheap
> enough in order to get rid of untrusted certificates? 

The certificate is fine, the actual problem is that mail.cloud9.net does
not include the intermediate issuer certificate in its certificate
chain, which consists of justs the leaf certificate.  The issuer cert
for "Sectigo RSA Domain Validation Secure Server CA" would be needed to
complete the chain to a WebPKI trust anchor (root CA).

Sectigo sure go to a lot of trouble to make obtaining the intermediate
certificate a laborious process, I am attaching a copy, along with a
"just in case" cross-cert for its issuer.

> When reading the documentation page
> http://www.postfix.org/TLS_README.html#client_tls however I am
> wondering what the difference between options “verify” and “secure”
> is.

By default, "verify" checks whether the presented certificate matches
the MX hostname, which is typically obtained via unauthenticated DNS
lookups, so easily subject to active (MiTM) attacks.

With "secure" the presented certificate is checked agains the nexthop
domain (typically the domain part of the recipient address).  This is
not subject to attacks via forged DNS replies.  However, typically
the MX host certificate will not have the recipient domain as one
of its SANs unless the domain is self-hosted.

For example, "postfix.org" does not appear in the certificate of
"mail.cloud9.net".  So "secure" is often not an option, unless
you specify explicit non-default matching criteria, at which
point the difference between "secure" and "verify" vanishes,
they only differ in the default name matching patterns.

> I read it several times and got the message, I should not use
> either, but what exactly is the difference remained unclear to me. Is
> “DNS forgery resistant server certificate verification“ defined in
> some RFC or other document I am not aware of?

It is defined (explained) in TLS_README.  Sorry it was not as clear as
you would like.

-- 
    Viktor.
subject=C = GB, ST = Greater Manchester, L = Salford, O = Sectigo Limited, CN = 
Sectigo RSA Domain Validation Secure Server CA
issuer=C = US, ST = New Jersey, L = Jersey City, O = The USERTRUST Network, CN 
= USERTrust RSA Certification Authority
-----BEGIN CERTIFICATE-----
MIIGEzCCA/ugAwIBAgIQfVtRJrR2uhHbdBYLvFMNpzANBgkqhkiG9w0BAQwFADCB
iDELMAkGA1UEBhMCVVMxEzARBgNVBAgTCk5ldyBKZXJzZXkxFDASBgNVBAcTC0pl
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00u/I5sUKUErmgQfky3xxzlIPK1aEn8=
-----END CERTIFICATE-----

subject=C = US, ST = New Jersey, L = Jersey City, O = The USERTRUST Network, CN 
= USERTrust RSA Certification Authority
issuer=C = GB, ST = Greater Manchester, L = Salford, O = Comodo CA Limited, CN 
= AAA Certificate Services
-----BEGIN CERTIFICATE-----
MIIFgTCCBGmgAwIBAgIQOXJEOvkit1HX02wQ3TE1lTANBgkqhkiG9w0BAQwFADB7
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-----END CERTIFICATE-----

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