Hello again,

On 04/23/2018 06:55 PM, Viktor Dukhovni wrote:
>> 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.

Correct. Thank you.


>> 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

I already narrow the scope as you recommend: outlook servers get
'reject_authenticated_sender_login_mismatch', all others get
'reject_sender_login_mismatch'.
We already DKIM-sign outbound email. I have to check if those signatures
remain valid after going through Office365 servers (I think so).


> 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.


Got any pointers on how to do this? What should I put in my to-read list
next?

Thank you again.
Best regards,
Mário Barbosa

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