Viktor Dukhovni via Postfix-users wrote in
 <z6-j2wjhqckn8...@chardros.imrryr.org>:
 |On Fri, Feb 14, 2025 at 06:13:51PM +0000, Matt Selsky via Postfix-users \
 |wrote:
 |>> Email with:
 |>>     From: "whatever" <f...@example.com>, <b...@example.org>
 |> 
 |> Exchange rejects this.
 |
 |But it is valid RFC5322 syntax.
 |
 |    https://datatracker.ietf.org/doc/html/rfc5322#section-3.4
 |
 |        mailbox-list    =   (mailbox *("," mailbox)) / obs-mbox-list
 |
 |    https://datatracker.ietf.org/doc/html/rfc5322#section-3.6.2
 |
 |        from            =   "From:" mailbox-list CRLF
 |
 |Only Sender is required to be single-valued:
 |
 |        sender          =   "Sender:" mailbox CRLF
 |
 |So it is unclear that such rejection should be on unconditionally, or
 |even by default.

RFC 5322 explicitly requires the use of Sender: in the presence of
a From with multiple mailboxes, which is i think the problem of
the op.  (The BSD Mail clone i maintain then requires user
interaction, unless the variable *sender* is set, however
documents

 sender    An address that is put into the ‘Sender:’ field of outgoing
           messages, quoting the standard RFC 5322: the mailbox of the
           agent responsible for the actual transmission of the message.
           For example, if Mary sends a mail for Alice, then Alice should
           be in ‘From:’ whereas Mary should be present in ‘Sender:’.  Ac‐
           cording to the standard this variable must be set if from† con‐
           tains multiple addresses.  [v15 behaviour may differ] Expect
           automatic management of the from† and sender† relationship (re‐
           quiring an address order in the former).  alias†es are expanded

^ that the magic RFC5322.From is expected to be sorted in the
future, so that the first entry can be used as Sender:, ie, what
is implicitly used by DKIM for that purpose...)

           instantly with senders kept; Contextually this address is a
           member of alternates†.  Also see -r†, r-option-implicit†.

--steffen
|
|Der Kragenbaer,                The moon bear,
|der holt sich munter           he cheerfully and one by one
|einen nach dem anderen runter  wa.ks himself off
|(By Robert Gernhardt)
|
|In Fall and Winter, feel "The Dropbear Bard"s pint(er).
|
|The banded bear
|without a care,
|Banged on himself for e'er and e'er
|
|Farewell, dear collar bear
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