The curious case of seemingly random SPF failures in an Exchange Hybrid

Or "How I found out about - Tenant Attribution - and what the heck it is..." An email gets send from our on-premises environment (or comes to our on-premises via the hybrid servers...). Since we're using mail gateways, Exchange routes this message to the mail gateways living in the DMZ The mail gateways do their DNS lookup, see that the mail should be routed to EOP, and establish a connection to deliver the mail (TLS secured, since this is enabled on the mail gateways!) EOP receives the message, goes throught its rule list and delivers the message to Exchange Online Exchange Online delivers the message to the intended recipient...

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Changes to Office 365

Microsoft, in all its wisdom, announced a number of improvements to the service to help reduce cost, increase security, and boost employee productivity.

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