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Microsoft 365 Direct Send Abuse: Phishing Risks & Security Recommendations

Medium
Published: Mon Aug 18 2025 (08/18/2025, 14:16:17 UTC)
Source: AlienVault OTX General

Description

Threat actors are actively exploiting Microsoft 365's Direct Send feature to deliver phishing emails, bypassing perimeter security solutions by routing malicious messages through trusted infrastructure. This technique requires no credentials, only knowledge of the target domain and valid recipient addresses. The attack process involves identifying organizational domains, crafting emails impersonating internal users, and delivering them through Microsoft 365's infrastructure. Recent campaigns have successfully harvested credentials and established footholds within targeted environments. Attackers use automated tools to generate convincing business-themed lures, often utilizing PDF and DOCX attachments with QR codes or obfuscated HTML leading to phishing pages. The abuse of Direct Send represents a critical gap in email security defenses, particularly for organizations relying heavily on email communications.

AI-Powered Analysis

AILast updated: 08/18/2025, 14:47:53 UTC

Technical Analysis

The threat involves malicious actors exploiting the Microsoft 365 Direct Send feature to conduct phishing campaigns that bypass traditional perimeter email security controls. Direct Send is designed to allow organizations to send emails from internal devices or applications directly through Microsoft 365 infrastructure without requiring SMTP authentication credentials. Attackers leverage this by identifying target organizational domains and valid recipient email addresses, enabling them to craft emails that appear to originate from internal users or trusted sources within the organization. This technique does not require stolen credentials, only knowledge of the target domain and recipient addresses, making it accessible to a wide range of threat actors. The attack process typically involves reconnaissance to identify organizational domains and valid email addresses, followed by the creation of convincing phishing emails that often include business-themed lures. These emails frequently contain PDF or DOCX attachments embedded with QR codes or obfuscated HTML that redirect victims to phishing websites designed to harvest credentials or deliver malware. Because the emails are routed through Microsoft 365's trusted infrastructure, they can evade many traditional email security solutions that rely on external reputation or sender verification checks. Recent campaigns exploiting this technique have successfully harvested credentials and established footholds within targeted environments, facilitating further compromise such as business email compromise (BEC) and lateral movement. The abuse of Direct Send represents a critical gap in email security defenses, especially for organizations heavily reliant on Microsoft 365 for email communications. The threat is compounded by the use of automated tools to generate highly convincing phishing content, increasing the likelihood of victim interaction and successful exploitation.

Potential Impact

For European organizations, this threat poses significant risks to confidentiality, integrity, and operational continuity. Credential theft via phishing can lead to unauthorized access to sensitive corporate data, intellectual property, and personal data protected under GDPR, potentially resulting in regulatory penalties and reputational damage. The ability to bypass perimeter defenses increases the likelihood of successful phishing attacks, undermining trust in internal communications and complicating incident detection and response. Furthermore, compromised credentials can enable attackers to conduct business email compromise, financial fraud, and lateral movement within networks, escalating the severity of breaches. Given the widespread adoption of Microsoft 365 across Europe, the scale of potential impact is substantial, affecting organizations of all sizes and sectors, including finance, healthcare, government, and critical infrastructure.

Mitigation Recommendations

1. Implement strict SPF, DKIM, and DMARC policies with enforcement to reduce spoofing risks and improve email authentication. 2. Monitor and restrict the use of Microsoft 365 Direct Send by limiting allowed IP addresses and devices that can send emails via this method. 3. Employ advanced email security solutions that analyze email content and attachments for phishing indicators, including sandboxing of attachments and URL rewriting. 4. Enable multi-factor authentication (MFA) across all user accounts to mitigate the impact of credential theft. 5. Conduct regular user awareness training focused on recognizing phishing attempts, especially those leveraging internal-looking emails and attachments with QR codes or obfuscated content. 6. Utilize Microsoft Defender for Office 365 features such as Safe Links and Safe Attachments to detect and block malicious content. 7. Implement continuous monitoring and anomaly detection for unusual email sending patterns or login behaviors indicative of compromise. 8. Regularly review and audit email flow rules and connectors in Microsoft 365 to identify and close any misconfigurations that could be abused. 9. Establish incident response playbooks specifically addressing phishing and credential theft scenarios involving Microsoft 365. 10. Collaborate with threat intelligence providers to stay updated on emerging phishing campaigns exploiting Direct Send.

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Technical Details

Author
AlienVault
Tlp
white
References
["https://www.mimecast.com/threat-intelligence-hub/microsoft-direct-send-abuse/"]
Adversary
null
Pulse Id
68a335b16810180f68852d39
Threat Score
null

Indicators of Compromise

Ip

ValueDescriptionCopy
ip139.28.38.90
ip141.95.114.238
ip141.95.71.216
ip23.163.0.158
ip51.89.87.86

Hash

ValueDescriptionCopy
hashe9dc9f962eb17f59d5dc9f55e0784f01
hash01b60a616a0c66a549323c2a0bb3262f5afe6e82
hash0736b07c27ff2ff21175991c2ffae38d75a66bbb57fe4390afb3347e4d6e691a
hash092d0be4a754532ad49e202eeba2a7709dad03f3f58cf72205f38efc668ebabd
hash19279573e2c3b0e6348bb305e3101531eea978037330636942a0be85dccd62c1
hash3432411a3bb498e6688d24dc3824b6469242d42d0b8742116479f35a8c05ab5a
hash3f52227acb6f97853b491cdaab53630cb21b3337a972efcb05660cd139df2482
hash48171e699562fe854418797cd8b8517b3f5eec598fd89e3d20c5a8f346176bf2
hash5b6aa8f966e240f620ad10417ff4804941966f878cc83020391ad786f5360f43
hash625561c24491e8b68efa34e14c5a332c63c6121a333f700af4ff6801ebe587c8
hash7c11352b17e325a53e3a73e34459fc55b90ceaf2c3cd4dc4421be879c7147391
hash975b04bb26d5fe627e195bdf46fc4eec7b25b63d7b4ab926b437a04903ec522f
hash988d3069d1241d2784debeb6946c57a8c66221d7fbfbd6228b2b8b3cc4e92a50
hashb810f7e999d5824147535e3974cf349010f78badaa0428c554bb3e5eec56db2f
hashb96ee4c2bdf566a5740dc100cf1c70896cd2806fac42d46b022d5c52c3a8a52a
hashc2394537d5e7b3c1c9afc73408b5c6b1c1154650a4a8454b9f4e534c9ddbd092
hashca82e7201694b964e0f6702e08f75f98f0732552aefaed6ae8b170689341bfe2
hashcc2f055a242eec9ba870fc3040883439666266a018c833b72bb201592ff0c0e4
hashcf74d4c1c3e8317c43aacdcda57cb8da032477e24732d0a7987c8bf5aa9ff186
hashd5800e021a88c6e91f1605b892e8aefe1ba21719022417746a64a4acba13e903
hashdf6bc150a77c36beafbfd0c59daa7a8960bb090743b778477e25805195640c0c
hashf24785156ec9c045e88eed48b2a262996a12e7bc62f50784bba9334172668275

Domain

ValueDescriptionCopy
domaindjvzk.uekmu.es
domainjmvthr.owlrd.ru

Threat ID: 68a33999ad5a09ad00af08fd

Added to database: 8/18/2025, 2:32:57 PM

Last enriched: 8/18/2025, 2:47:53 PM

Last updated: 8/18/2025, 2:47:53 PM

Views: 2

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