Just don’t play with connectors and mail flow in an attempt to bypass 365’s spam filter
Todays painful lesson, 365 is a fickle beast when it comes down to the routing of emails. Especially when trying to circumvent their built in protection by the use of connectors and rules.
Exchange Online Protection (EOP) is the cloud-based filtering service that protects your organization against spam, malware, and other email threats. EOP is included in all Microsoft 365 utilizing Exchange Online mailboxes.

Now to clarify this can be worked around if you know what your doing but as your buying a service from Microsoft they are entitled to protect their service. This includes from abuse down to poor or misconfiguration, an example of working around EOP would need a Mail Transfer Agent (MTA) capable of adding headers to the messages as it passes them (see below)

Moral of the story, you cant fix what ain’t broken
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