I have performed some tests of this "External" call out feature. I have sent test messages to myself, using an external unauthorized SMTP-relay server, spoofing the From address as a coworker's SMTP-address. Even though the messages are clearly inbound, neither Outlook nor OWA applies the "External" call out to the messages. When I look at the headers of these incoming messages, the SPF, DKIM, and DMARC tests fail, as expected. The X-MS-Exchange-Organization-MessageDirectionality value is Incoming. The X-MS-Exchange-OrganizatonAuthAs value is Anonymous. Yet Outlook and OWA still do not apply the "External" call out to the messages.
This is obviously a crucial scenario for the "External" call out to be applied....perhaps more crucial than any other scenario.
Has anyone else tested this feature?