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Professional red teaming : conducting successful cybersecurity engagements
Oakley J., Apress, New York, NY, 2019. 232 pp. Type: Book (978-1-484243-08-4)
Date Reviewed: Feb 20 2020

Technical books about red teaming, or ethical hacking in general, run the risk of being outdated by the time they get published. New threats will have occurred, for example, making the attack specifics invalid. Thus, the author of this book has chosen an approach that focuses on the underlying processes to follow when performing offensive security engagements. The book therefore clearly aims to supplement the already existing body of literature describing the technical aspects of ethical hacking.

After an overview of red teaming, the author makes a strong case for human involvement during ethical hacking. While automated tools are often necessary to do the groundwork, they can easily miss important clues, such as significant names of servers and other elements of the information technology (IT) landscape.

The next chapter describes many practical challenges the red team can face, and for those working in the field, they will be quite recognizable. The author provides useful suggestions on how to overcome the various obstacles, including IT personnel who won’t cooperate, management that tries to influence the scope of attack, and so on.

The fourth chapter expands on the scope, or as the author calls it, the shaping of the engagement. Given that most red teams work under strict budget and time restrictions, setting and sticking to the correct scope is crucial to success. The author’s examples reflect wide and deep experience, which helps the reader to deal with possible setbacks and other complications that can arise during the red teaming exercises.

Among the most important elements of any red teaming effort are the rules of engagement (ROE), which outline what is allowed during the exercise and what is off limits. Rightfully, the author dedicates a whole chapter to ROE. It would have been helpful for the book to include a template ROE; however, by reading between the lines, the attentive reader should be able to pick up the essential paragraphs that must be included.

The next chapter deals with the execution phase and suddenly takes a deep dive into note taking with highly technical examples. Certainly, the material is useful because it makes the topic come alive. However, a novice reader might be intimidated and left with a feeling of bewilderment about all those mysterious screen shots.

Chapter 7 covers the reporting phase, and the author includes all the relevant elements of good reporting, including the often-overlooked paragraphs on remediation of found weaknesses and how to report nonfindings. In chapter 8, the author describes the challenges associated with purple team testing, which is a situation where ethical hackers (the red team) work closely with the existing security (or defense) team: the blue team. Most issues arise from people problems, as the author calls it, and like most of his book, the examples mentioned are highly recognizable and the suggested steps equally useful.

The remainder of the book introduces readers to the concept of counter advanced persistent threat (APT) red teaming, or CAPTR teaming. This approach was inspired by the fact that malicious hackers are not restrained by ethical, operational, or funding limits. Thus, to mimic a real attack, ethical hackers should, as the author states, “cheat the typical process.” What follows is an approach that aims to maximize efforts, in the least amount of the given time for the assignment, by focusing on the most important targets. Instead of an overall security assessment, the CAPTR teaming approach suggests going directly after those areas of the target that are most critical.

Given that the author spends a lot of pages describing the CAPTR teaming method, which is arguably more efficient than traditional ethical hacking approaches, it is a missed opportunity to not include the more passive methods of security evaluation. Most findings resulting from ethical hacking exercises, as the author points out, can be grouped into two categories: misconfigurations and missing updates/patches. Given this expected outcome, would it not be more efficient and possibly faster to go straight to the sources of security vulnerabilities and review the target for missing patches and updates, as well as carefully review the existing configuration for suboptimal settings?

In conclusion, this highly fascinating read makes the work of ethical hackers come alive with many real-life examples. The included tips, suggestions, and practical advice make it a welcome addition to the existing books about red teaming and ethical hacking.

More reviews about this item: Amazon

Reviewer:  Riemer Brouwer Review #: CR146900 (2008-0188)
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