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Hackers Abuse Microsoft 365’s Direct Send Feature to Deliver Internal Phishing Attacks

Posted on August 2, 2025August 2, 2025 By CWS

Cybercriminals have found a complicated new assault vector by exploiting Microsoft 365’s Direct Ship characteristic to ship phishing campaigns that masquerade as legit inner communications.

This rising menace leverages a legit Microsoft service designed for multifunction printers and legacy purposes, turning it right into a weapon for social engineering assaults that bypass conventional e mail safety controls.

The assault marketing campaign represents a major evolution in phishing ways, as menace actors can now ship malicious emails that seem to originate from inside the goal group with out requiring legitimate credentials or authentication.

By exploiting Direct Ship’s inherent belief mannequin, attackers obtain unprecedented credibility of their phishing makes an attempt, making detection and prevention significantly more difficult for safety groups.

Proofpoint researchers recognized this lively marketing campaign concentrating on Microsoft 365 tenants via a fancy infrastructure involving unsecured third-party e mail safety home equipment and digital personal server property.

The subtle operation demonstrates how cybercriminals proceed to weaponize legit cloud companies to evade detection and enhance the success fee of their social engineering campaigns.

Technical Assault Infrastructure and Message Injection Circulate

The assault mechanism follows a rigorously orchestrated four-step course of that exploits a number of layers of e mail infrastructure.

Attackers initially set up connections to digital hosts working Home windows Server 2022 via Distant Desktop Protocol on port 3389, offering them with a legit Home windows setting for his or her operations.

Assault movement (Supply – Proofpoint)

From these compromised hosts, they provoke SMTP connections to unsecured third-party e mail safety home equipment hosted by regional Infrastructure-as-a-Service suppliers.

These compromised home equipment function SMTP relays, that includes legitimate DigiCert SSL certificates and supporting AUTH PLAIN LOGIN with STARTTLS encryption.

Nonetheless, the home equipment expose weak ports 8008, 8010, and 8015 with expired or self-signed certificates, creating safety gaps that attackers exploit.

The malicious messages are then relayed via these home equipment on to Microsoft 365 tenants, the place they’re delivered through Direct Ship utilizing spoofed inner sender addresses.

Organizations can implement fast safety by executing the PowerShell command Set-OrganizationConfig -RejectDirectSend $true to disable Direct Ship performance.

Moreover, monitoring message headers for composite authentication failures marked as compauth=fail can assist determine these subtle spoofing makes an attempt earlier than they attain finish customers.

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Cyber Security News Tags:365s, Abuse, Attacks, Deliver, Direct, Feature, Hackers, Internal, Microsoft, Phishing, Send

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