Consider a pre-generated text file sample.eml like this one:

  From: Bob <bo...@example.com>
  To: al...@example.org
  Subject: foobar

  The message body goes here...

Imagine further that Bob is logged in as user123 on host.example.net
which runs Postfix, and Bob sends the message like so:

  $ /usr/sbin/sendmail -t < ~/sample.eml

This would typically result in an envelope sender address like
<user...@host.example.net>, which may not be reachable from the outside.
To force a different envelope sender address, Bob could use the
following:

  $ /usr/sbin/sendmail -t -r bo...@example.com < ~/sample.eml

This can of course be automated by extracting the "From:" header value
from sample.eml, e.g. in a wrapper script which then calls sendmail with
the appropriate "-r ..." parameter.

I wonder however if this is something which sendmail can achieve out of
the box, without the need for a wrapper script? The sendmail(1) man page
doesn't seem to indicate that there are parameters for this use case,
but I thought I'd ask here.

By the way, I have considered sender_canonical_maps, but if each userNNN
can use several different valid From: addresses (all valid), canonical
address rewriting does not seem like the right tool?

-Ralph
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