SMTP Pentest Guide

Email Authentication Attacks

Email authentication attacks exploit weaknesses in email authentication mechanisms to send spoofed emails that appear to come from legitimate domains.

This section covers various techniques for bypassing email authentication mechanisms such as SPF, DKIM, and DMARC, as well as other email spoofing techniques.

Email Authentication Overview

Email authentication mechanisms are designed to prevent email spoofing and phishing attacks by verifying that emails come from legitimate sources. The three main email authentication mechanisms are:

  • SPF (Sender Policy Framework): Verifies that the sending server is authorized to send email for the domain in the From header
  • DKIM (DomainKeys Identified Mail): Verifies that the email was cryptographically signed by the domain in the From header
  • DMARC (Domain-based Message Authentication, Reporting, and Conformance): Verifies that the email passes SPF and/or DKIM checks and that the From header domain aligns with the authenticated domain

Despite these mechanisms, there are various techniques that attackers can use to bypass email authentication and send spoofed emails.

DKIM Bypass
Techniques for bypassing DKIM email authentication

This attack focuses on bypassing DomainKeys Identified Mail (DKIM) email authentication to send spoofed emails that appear to come from a legitimate domain.

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SPF Bypass
Techniques for bypassing SPF email authentication

This attack focuses on bypassing Sender Policy Framework (SPF) email authentication to send spoofed emails that appear to come from a legitimate domain.

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Header Manipulation
Exploiting email header manipulation techniques

This attack involves manipulating email headers to bypass authentication mechanisms and create convincing spoofed emails.

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Authentication Results Injection
Exploiting Authentication-Results headers in email

This attack involves injecting fake Authentication-Results headers into emails to make them appear to have passed authentication checks when they haven't.

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Parsing Inconsistencies
Exploiting email parsing inconsistencies

This attack exploits inconsistencies in how different email systems parse and interpret email headers and content, allowing attackers to craft emails that appear differently to different systems.

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Service Account Spoofing
Exploiting service accounts for email spoofing

This attack exploits legitimate service accounts or third-party services that are authorized to send emails on behalf of a domain.

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Replay & Multiple From
Exploiting email replay and multiple From headers

This attack combines email replay techniques with multiple From headers to create sophisticated spoofing attacks that can bypass authentication mechanisms.

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General Mitigation Strategies

To protect against email authentication attacks, organizations should implement a comprehensive email security strategy that includes:

  • Implement all three authentication mechanisms: Use SPF, DKIM, and DMARC together for maximum protection
  • Use strict policies: Configure SPF and DMARC with strict policies (e.g., -all for SPF, p=reject for DMARC)
  • Monitor authentication failures: Use DMARC reporting to monitor authentication failures and adjust policies accordingly
  • Train users: Educate users about the risks of email spoofing and phishing
  • Use email security solutions: Implement email security solutions that can detect and block spoofed emails
  • Regularly audit configurations: Regularly audit SPF, DKIM, and DMARC configurations for weaknesses
  • Stay informed: Stay informed about new email authentication attacks and mitigation strategies