Email security: attack and defence
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Email security: attack and defence

About the Book

This book is for curious people that want to know how email security works, how to attack email protocols and how to defend from such attacks. It does not matter what your role is or if you do not work in IT security at all. I believe it can be of particular use for both people that have the email security of an organization to care for (e.g. security engineers, network and system administrators) and people that attack it for a living (e.g. red teamers and pentesters).

It is divided in three main topics:

  • A presentation of email security mechanisms
  • A set of attacks
  • A proposal for defense

The content is technical and use practical examples. All attacks described have been performed by the author (me) and part of it is based on professional penetration tests. Exercises are available at each chapter to familiarize the reader with hands-on cases.

About the Author

Jeffrey Bencteux
Jeffrey Bencteux

Jeffrey is an IT security engineer currently working as a pentester. He has over seven years of field experience in cybersecurity, dealing with complex problems and people.

His research subjects are mainly network security, email security, cloud security and <whatever> security really.

You can find his blog here:

Table of Contents

    • Introduction
      • A few words before beginning
      • Greetings
      • Credits
      • Feedback
    • Email security mechanisms
      • Encrypting communications
      • Sender Policy Framework (SPF)
      • DomainKeys Identified Mail (DKIM) Signatures
      • Domain-based Message Authentication, Reporting, and Conformance (DMARC)
      • Authenticated Received Chain (ARC)
      • Brand Indicators for Message Identification (BIMI)
      • A real-life example
      • Exercises
    • Attack
      • Tooling
      • Fingerprinting
      • TLS downgrade
      • S/MIME & OpenPGP implementations
      • SPF: allow by default
      • SPF: Attacking third-parties in include
      • SPF: Attacking marketing platforms
      • From subdomain takeover to phishing emails
      • Forging DKIM signatures
      • DMARC: loose policy and subpolicy
      • DMARC: poor sampling percentage
      • Further reading
      • Exercises
    • Defence
      • Concepts
      • A (relatively) secure mail infrastructure
      • Priority list
      • Exercises
    • Conclusion
    • Exercises solutions
      • Email security mechanisms
      • Attack
      • Defence

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