On Wed, Sep 10, 2025 at 11:52:03AM +0200, Matus UHLAR - fantomas via 
Postfix-users wrote:
> On 08.09.25 18:37, John, Chris via Postfix-users wrote:
> > I have a postfix 3.5.2 system that accepts messages from internal hosts
> > and relays to internal destinations and to an email perimeter that
> > delivers to external (Internet) domains.
> > 
> > The issue I'm seeing is regarding external domains that do not follow
> > DNS best practices and have CNAME records published for the same domain
> > that their MX records are published for.
> 
> This is not about following best practices. This is clearly violation of DNS

No, not a violation of DNS, rather such a rewrite is a violation of
RFC2321 (and its successors: 5321, 5321bis[1]) which changed the
semantics of CNAME-valued address domain parts from RFC821.

RFC821, Section 3.7 "Domains" reads in part:

    Whenever domain names are used in SMTP only the official names are
    used, the use of nicknames or aliases is not allowed.

Whereas RFC2821, Section 3.6 "Domains" reads in part:

    https://www.rfc-editor.org/rfc/rfc2821#section-3.6

    Only resolvable, fully-qualified, domain names (FQDNs) are permitted
    when domain names are used in SMTP.  In other words, names that can
    be resolved to MX RRs or A RRs (as discussed in section 5) are
    permitted, as are CNAME RRs whose targets can be resolved, in turn,
    to MX or A RRs.  Local nicknames or unqualified names MUST NOT be
    used.

The distinction being that <localpart@alias.example> was therefore permitted.

Sufficiently ancient Sendmail configurations defaulted to "canonifying"
the recipient domain.  I had a vague recollection the syntax was
something like $[ ... ].  Which was almost correct, a quick search turns
up:

    https://www.sendmail.org/~ca/email/doc8.12/cf/m4/features.html

    nocanonify  Don't pass addresses to $[ ... $] for canonification by
                default, i.e., host/domain names are considered canonical,
                except for unqualified names, which must not be used in this
                mode (violation of the standard).

A properly configured Sendmail system should not "canonify", but it
seems that some still do.

-- 
    Viktor.  🇺🇦 Слава Україні!

[1] https://datatracker.ietf.org/doc/html/draft-ietf-emailcore-rfc5321bis-44
    This will soon be published as a "full internet standard" (STDnnnn),
    rather "merely" a "proposed standard" as with most standards-track
    RFCs.  It took only ~50 years for SMTP to be "standardised". :-)
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