The Cybersecurity Canon: Metasploit: The Penetration Tester’s Guide

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We modeled the Cybersecurity Canon after the Baseball or Rock & Roll Hall-of-Fame, except for cybersecurity books. We have more than 25 books on the initial candidate list, but we are soliciting help from the cybersecurity community to increase the number to be much more than that. Please write a review and nominate your favorite

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Book Review by Canon Committee Member, Brian Kelly: Metasploit: The Penetration Tester’s Guide (2011) by David Kennedy, Jim O’Gorman, Devon Kearns, and Mati Aharoni

Executive Summary

Learning to think like a criminal, or in this case a cybercriminal, is a requirement for all penetration testers. Fundamentally, penetration testing is about probing an organization’s systems for weakness.
While the goal of Metasploit: The Penetration Tester’s Guide is to provide a useful tutorial for beginners, it also serves as a reference for practitioners.

The authors write in the Preface that, “This book is designed to teach you the ins and outs of Metasploit and how to use the Framework to its fullest.” While the book is focused on using the Metasploit Framework, it begins by building a foundation for penetration testing and establishing a fundamental methodology.

Using the Metasploit Framework makes discovering, exploiting, and sharing vulnerabilities quick and relatively painless. While Metasploit has been used by security professionals for several years now, the tool can be hard to grasp for first-time users. This book fills the gap by teaching readers how to harness the Framework and interact with the active community of Metasploit contributors.

While the Metasploit Framework is frequently updated with new features and exploits, the long-term value of this book is its emphasis on Metasploit fundamentals, which, when understood and practiced, allow the user to be comfortable with both the frequent updates of the tool and also the changing penetration testing landscape.

Review

Metasploit: The Penetration Tester’s Guide is laid out in two sections, Chapters 1 to 5 introduce the basics of penetration testing and the Metasploit framework with the remaining 11 chapters outlining specific areas of the framework, building on the fundamental concepts introduced in the first section. The bulk of the book takes the penetration tester through using the framework with examples of both use cases and the syntax required. The examples begin with the very basics techniques of the craft and move through carrying out exploits and gaining value from the post-exploitation capabilities of Meterpreter.

The authors give a short overview of each topic before jumping right into the hands on – showing readers the commands to use and then dissecting the output – explaining step by step what is happening and what was accomplished. The book allows readers to move quickly from the basics of penetration testing through using the platform to perform the different phases of intelligence gathering and exploitation.

The exploitation sections cover a wide range of techniques, including attacking MS SQL, dumping password hashes, pass the hash and token impersonation, killing antivirus, and gathering intelligence from the system to pivot deeper into the target network.

Conclusion

Metasploit: The Penetration Tester’s Guide is written in a hands-on, tutorial-like style that is great for beginners, as well as folks who prefer to learn by doing. This is an excellent book for anyone interested in a hands-on learning approach to cybersecurity and the fundamentals of penetration testing. It is also a great reference book for the seasoned Metasploit user and those new to Metasploit who want a step-by-step instruction manual.

The craft of penetration testing is covered deeply and broadly. However, the book’s greatest source of value is how the concepts being applied are explained and demonstrated with well-annotated examples. The authors’ experiences in formal instruction and practice are evident. This book achieves a good balance between concept and practicality.

The goal of the Cybersecurity Canon is to identify a list of must-read books for all cybersecurity practitioners — be they from industry, government or academia — where the content is timeless, genuinely represents an aspect of the community that is true and precise, reflects the highest quality and, if not read, will leave a hole in the cybersecurity professional’s education that will make the practitioner incomplete. Finally, the books must provide timeless technical know-how. Metasploit: The Penetration Tester’s Guide achieves these goals, and I believe it is worthy of inclusion in the Cybersecurity Canon candidate list. It is a valuable resource for all cybersecurity professionals’ libraries, whether they be novices or experienced practitioners.

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