Like others I have been facing problems with outlook blocking emails from my servers from time to time. I am experimenting with transport maps but the only viable solution I have found is very messy and time consuming*.
I am using sendgrid (Brevo now) and have authenticated my domains there.
What I want to accomplish is provide a server-wide (not per domain) routing for microsoft domains destinations.
From what I gather this can only be done via
custom_transport.pcre, so I edited it to
and setup the corresponding Sender-dependent transport for its credentials via the GUI but I get error
said: 530 Error: authentication Required (in reply to MAIL FROM command)
when trying to send to such destinations.
I can’t figure out what I’m doing wrong.
* The solution that works is to create an account on a spare domain (I have some unused), allow it to send as ANY account on the server and create 2 Sender-dependent transports:
- The sendgrid one to be used by the spare domain
- One pointing to postfix:587 using the spare domain’s account
And also setup the Transport Maps for the Microsoft domains via the GUI. So 2 relays, 1 internal and 1 external ^^