On 17.10.2025 at 10:54 Rodolfo Saccani via mailop wrote:

> We are detecting hundreds of thousands of malicious messages originated by 
> M365 using this schema:
>
> - The attacker creates a hybrid tenant on 365
> - The attacker configures the tenant to use the outbound gateway of the 
> victim (a 365 customer who does not cooperate in validating the outbound 
> gateway)
> - The attacker sends fake bounces (empty envfrom) spoofing the header-from 
> domain of the victim
>
> My personal assumption has always been that this kind of spoofing of another 
> Microsoft customer’s domain was not possible on 365.

Hello Rodolfo,

Graeme has already mentioned Echospoofing, many other ways have been described 
in the past on how to spoof sender domains from large email service providers 
including Microsoft:
- SMTP smuggling
- Message forwarding (https://arxiv.org/pdf/2302.07287.pdf)
- Authentication weaknesses 
(https://www.usenix.org/system/files/sec21-shen-kaiwen.pdf)
- or simply that Microsofts Outlook intentionally spoofs the From header when 
forwarding meeting invites.

Some of those problems have been fixed, but large and complex collaboration 
platform like Office365 offer a lot of possibilities for loopholes.

I would go with the old programming paradigm: Never rely on information which 
you receive from others to be clean, correct or consistent.

--
BR Oliver
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