Metasploit The Penetration Testers Guide Book Review

Wednesday, July 4, 2012 Posted by Corey Harrell

A penetration test is a method to locate weaknesses in an organization’s network by simulating how an attacker may circumvent the security controls. The Preface indicated Metasploit The Penetration Tester’s Guide was written specifically so “readers can become competent penetration testers”. The book further goes on to describe a penetration tester as someone who is able to find ways in which a “hacker might be able to compromise an organization’s security and damage the organization as a whole”. I’ve occasionally seen people talk about the book favorably but their comments were as it related to penetration testing. I wanted to review Metasploit The Penetration Tester’s Guide from a different angle; from the Digital Forensic and Incident Response (DFIR) perspective. As a DFIR professional it is important to not only understand the latest attack techniques but it’s equally important to be aware of what artifacts are left by those techniques. This is the perspective I used when reviewing the book and I walked away thinking. If you want to bring your Digital Forensic and Incident Response skills to the next level then throw Metasploit in your toolbox and work your way through this book.

From Methodology to Basics to Exploitation

The book starts out discussing the various phases to a penetration test which were: pre-engagement interactions, intelligence gathering, threat modeling, exploitation, and post exploitation. After covering the methodology there was an entire chapter dedicated to Metasploit basics. I liked how the basics were covered before diving into the different ways to perform intelligence gathering with the Metasplot framework. Not only did the intelligence gathering cover running scans using the Metasploit built-in scanners but it also discussed running scans with nmap and then building a database with Metasploit to store the nmap scans. Before getting into exploitation an entire chapter was dedicated to using vulnerability scanners (Nessus and Nexpose) to identify vulnerabilities in systems. After Chapter 4 the remainder of the book addresses exploitation and post-exploitation techniques. I liked how the book discussed simpler attacks before leading up to more advanced attacks such as client-side, spear phishing, web, and SQL injection attacks. The book even talked about some advanced topics such as building your own Metasploit module and creating your own exploits. I think the book fulfilled the reason for which it was designed: to “teach you everything from the fundamentals of the Framework to advanced techniques in exploitation”.

Prepare, Prepare, and Prepare

Appendix A in the book walks you through setting up some target machines. One of which is a vulnerable Windows XP box running a web server, SQL server, and a vulnerable web application. Setting up the target machines means you can try out the attacks as you work your way through the book. I found it a better learning experience to try things out as I read about them. One addition benefit to this is that it provides you with a system to analyze. You can attack the system then examine afterwards to see what artifacts were left behind. I think this is a great way to prepare and improve your skills to investigate different kinds of compromises. Start out with simple attacks before proceeding to the more advanced attacks.

This is where I think this book along with Metasploit can bring your skills to the next level. There are numerous articles about how certain organizations were compromised but the articles never mention what artifacts were found indicating how the compromise occurred. Does the following story sound familiar? Media reports said a certain organization was compromised due to a targeted email that contained a malicious attachment. The reports never mentioned what incident responders should keep an eye out for nor does it provide anything about how to spot this attack vector on a system. To fill in these gaps we can simulate the attack against a system to see for ourselves how the attack looks from a digital forensic perspective. Spear-phishing attack vector is covered on page 137 and the steps to conduct the attack is very similar to how those organizations are compromised. The simulated attacks don’t have to stop at spear phishing either since the following could also be done: Java social engineering (page 142), client-side web exploits also known as drive-bys (page 146), web jacking (page 151), multipronged attack (page 153), or pivoting onto other machines (page 89) are a few possibilities one could simulate against the targeted machines. It's better to prepare ourselves to see these attacks in advanced then it is to wait until we are tasked with analyzing a compromised system.

Where’s the Vulnerability Research

Metasploit The Penetration Tester’s Guide is an outstanding book and is a great resource for anyone wanting to better understand how attacks work. However, there was one thing I felt the book was missing. The process to identify and research what vulnerabilities are present in specific software you want to exploit. The book mentions how Metasploit exploits can be located by keyword searches but it doesn’t go into detail about how to leverage online resources to help figure out what exploits to use. A search can be done online for a program/service name and version to list all discovered vulnerabilities in that program. Also, there is additional information explaining what a successful exploit may result in such as remote code execution or a denial of service. This approach has helped me when picking what vulnerabilities to go after and I thought a book trying to make competent penetration testers would have at least mentioned it.

Four Star Review

If someone wants to know how to better secure a system then they need to understand how the system can be attacked. If someone wants to know how to investigate a compromised system then they need to understand how attacks work and what those attacks look like on a system. As DFIR professionals it is extremely important for us to be knowledgeable about different attacks and what artifacts those attacks leave behind. This way when we are looking at a system or network it’s easier to see what caused the compromise; a spear phish, drive-by, SQL injection, or some other attack vector. I think the following should be a standard activity for anyone wanting to investigate compromises. Pick up Metasploit The Penetration Tester’s Guide, add Metasploit to your toolbox, and work your way through the material getting shells on test systems. You will not only have a solid understanding about how attacks work but you will pick up some pen testing skills along the way. Overall I gave Metasploit The Penetration Tester’s Guide a four star review (4 out of 5).

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