On 30.10.2024 at 08:59 Bo Frost Larsson via mailop wrote:

We are currently running Exchange in a hybrid setup and wish to send and 
receive mails "on-prem" and route it to Exchange Online (for those who have 
mailboxes there).



Inbound mail is fairly easy to set up. That's already done, and it works well.



What I would like to get your input on is how to (securely) relay mails from 
Exchange Online to people outside our organization. We are currently running 
all in- and outbound emails on postfix.



Exchange Online lists 4 ip-ranges as their outbound connectors:



40.92.0.0/15
40.107.0.0/16
52.100.0.0/14
104.47.0.0/17



I could just list those 4 ranges as "mynetworks" and that should work but I'm 
uncertain if Microsoft make any kind of "guaranties" that only their Exchange 
servers use those 4 ip-ranges. If I use the "mynetworks" then I'm worried that 
we'd be an open relay.



I thought about using "smtpd_client_restrictions" to limit who could relay 
through the server (besides a firewall) and adding our own domains to 
"check_sender_access". That way you would at least have to both send from the 
above-mentioned ranges, and we'd only allow you to send from our domains. I 
know that's not more than "security through obscurity" but it does raise the 
bar a little.

I wouldn’t do this, this is not secure. Restricting the sender addresses to 
your domain name makes it only slightly better, as your domain is also known to 
attackers and thus not very „obscure“. Multiple Proofpoint customers have been 
in the news lately for basically running open relays which accepted all 
messages from Exchange Online as internal emails.

I believe Microsofts designated way to do this is called „Centralized Mail 
Transport“: Exchange Online will send every outgoing message to your Exchange 
on premise, from where it will take the same route as your local mailboxes.
Additionally you have to make sure that your Exchange Online tenant rejects all 
incoming messages except those coming from your Exchange on premise. Just 
having the MX records point to your local Postfix is NOT enough, Exchange 
Online will still accept emails if someone tries to deliver them directly there 
- and attackers do try just that.
Also some special exceptions apply for mailboxes with forwarding rules and the 
various ways to set them up in Exchange.

If you don‘t want to use Centralized Mail Transport, I‘d configure Exchange 
Online to add a secret header to every outgoing message. Your local relay 
server then only accepts emails with this header, strips the header and 
dispatches the emails for final delivery.

—
BR Oliver
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