> On Apr 23, 2018, at 12:25 PM, mario.barbosa+postfixus...@gmail.com wrote:
> 
> Upon further inspection, I figured out what is probably obvious to you
> by now: the office 365 lists do not change the 'Sender:' header of the
> original message, and when it comes back to be delivered to its
> '@example.com' members, it bumps into...

Minor correction, the relevant address is the envelope sender, and
not any message header such as "Sender:".  The envelope is transmitted
separately alongside the message, but is not part of the message.

> smtpd_sender_restrictions =
>       permit_mynetworks,
>       reject_sender_login_mismatch,
>       check_policy_service unix:private/sender_policy_incoming
> 
> ... namely, that reject_sender_login_mismatch policy, because during the
> SMTP session the MAIL FROM is set by outlook.com servers as
> 'sending-u...@example.com' (and those servers have obviously not logged
> in as that user).

Correct.

> Temporarily, with help of 'smtpd_restriction_classes' and
> 'check_client_access' I have managed to relax the
> 'reject_sender_login_mismatch' requirement on mails coming from the
> office 365 servers, but I'd like to plug that hole as soon as possible.

Actually, that's about the best you can do, unless you sign the outbound
mail with DKIM *and* transit through Office365 does not invalidate those
signatures, *and* you narrow the scope of your current policy of rejecting
potentially forged sender addresses with:

   
http://www.postfix.org/postconf.5.html#reject_authenticated_sender_login_mismatch

and finally you implement some content or proxy filter that allows external
email from your domain if DKIM authenticated, and otherwise rewrites the
From: and/or Sender: address or (with proxy filter only) perhaps rejects
the message.

> So, my question to you is, what is the current best practice to deal
> with this?

Roughly what you're doing, unless you want to invest some real effort
to implement DKIM-based anti-spoofing.

-- 
        Viktor.

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