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This article details a specific phishing vector where attackers exploit the distinction between SMTP envelope senders and visible "From" headers to bypass Microsoft 365's Direct Send protections. By leaving the envelope sender blank, threat actors can deliver unauthenticated internal-looking emails that evade standard domain-based rejection controls without requiring stolen credentials. This represents a significant evolution in email impersonation tactics that challenges current infrastructure-level defenses within enterprise environments.

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Microsoft 365 Phishing Technique Uses Empty Envelope Sender to Evade Direct Send Blocking

Cybersecurity NewsSeptember 4, 20264 min read

Microsoft 365 users are facing a phishing technique built on a small change: attackers leave the SMTP envelope sender blank. The omission can let an unauthenticated message pass a Direct Send safeguard while showing employees an address that appears to belong to their own organization. The approach is not a Microsoft software flaw and does […] The post Microsoft 365 Phishing Technique Uses Empty Envelope Sender to Evade Direct Send Blocking appeared first on Cyber Security News.

Microsoft 365 users are facing a phishing technique built on a small change: attackers leave the SMTP envelope sender blank. The omission can let an unauthenticated message pass a Direct Send safeguard while showing employees an address that appears to belong to their own organization. The approach is not a Microsoft software flaw and does not need a stolen account. It exploits how Exchange Online’s RejectDirectSend control checks the domain in…

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