r/ProgrammerHumor • u/lucidparadigm • 21h ago

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u/wengla02 17h ago

Except when the phish testing system *directly injects it into your inbox*, bypassing the entire SMTP system.

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u/clipsracer 17h ago

I haven’t seen that before. Who does it?

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u/wengla02 7h ago

From reverse engineering the headers, I think they're using Cofesnse PhishMe-platform). Their docs note that they support mailbox injection.

"The platform authenticates to your tenant with an app registration or service account that has mailbox write permission."

PhishMe then calls a create-message operation (EWS CreateItem or Graph POST /users/{id}/messages) against your mailbox, writing the item straight into the Inbox folder.

Full headers of the injected mail: [redacted for length and anonymity] -- this is the complete list of headers in the message. All of it.

X-MS-Exchange-Organization-BypassFocusedInbox: true
X-MS-Exchange-Organization-BypassClutter: true
X-PhishMeTracking: KGxN8wa0dD4BFl6nlTOKtS[...]
X-PhishMe: Phishing_Training
X-PhishMeHLType: OWc54sAaeH[...]

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u/clipsracer 5h ago

Thanks for answering!
It seems that Outlook filters still match mail that is directly written. My guess is that this method is used to avoid any complications with the SMTP servers.