We are implementing a service that will encrypt email for our O365 mail tenant.
- RULE 1: If a specific pattern is found in the email SUBJECT, mail is sent to our mail encryption server and encrypted. Encrypted message is sent BACK to O365 with a Inbound/Receive Connector.
- RULE 2: It sends outgoing mail from specific senders through a particular smarthost.
The desired behavior is that when RULE 1 applies, the mail will be sent to the mail encryption server, which encrypts the mail and sends it BACK to O365 (via its configuration) -- then RULE 2 will kick in and send the encrypted mail outbound per usual.
Problem is that when both rules are turned on the new encryption rule (RULE 1) is being 'hit' in the message trace, but the message is still being sent outbound through the existing smarthost rule (RULE 2).
Its almost like O365 is choosing Rule 1 OR Rule 2 instead of processing Rule 1 AND Rule 2.
Is this the expected behavior of transport rules or am I missing something?