On Wed, Nov 23, 2022 at 12:19:19AM -0800, Dan Mahoney wrote:

> However, recently, outlook365 decided it did not like having
> secret-al...@support.dayjob.org as the To: envelope -- and we'd rather
> not have that in the headers either as well!

The solution is to not put the actual list address into the message
headers.

> Because we want fully mime-capable mail, sending with a script feels
> like the wrong answer.

Just put the list address in the Bcc: header, and put some "no-reply"
or some individual address in the "To:" line.  Long times ago the MH
mailer had an MUA that supported

    From: ...
    To: List Display Name: mailbox1, mailbox2, ...;
    ...

syntax and removed the mailbox addresses when sending, so that
the recipients would see:

    To: List Display Name: ;

Probably some folks still use MH, but not many I expect.

> Is there a good way to do this kind of forwarding, where it does
> proper putting of users into the to: header, perhaps even does VERP?

Configure a proxy recipient address that performs the necessary
transformations and resubmits via sendmail(1) with VERP enabled.

> Is there some kind of contributed script that can handle that
> expansion better than an alias :include:?

A Bcc to a :include: with an owner-alias does almost everything
you asked for, except for automatic VERP.

> Controlling who may *send* to such an alias/script is also a
> consideration.  Is there a good answer for that as well?

Configure the alias address at a domain for which you don't accept mail
via SMTP.  You could also configure it for a non-default Postfix
instance that does not accept any SMTP mail and has a short list of
"authorized_submit_users".  It would then be only available via
sendmail(1) to those users and with "-C /etc/postfix-mumble" to
specify the special instance (or same value in MAIL_CONFIG
environment).

-- 
    Viktor.

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