Book Image

Advanced Penetration Testing for Highly-Secured Environments: The Ultimate Security Guide

By : Lee Allen
Book Image

Advanced Penetration Testing for Highly-Secured Environments: The Ultimate Security Guide

By: Lee Allen

Overview of this book

The internet security field has grown by leaps and bounds over the last decade. Everyday more people around the globe gain access to the internet and not all of them with good intentions. The need for penetration testers has grown now that the security industryhas had time to mature. Simply running a vulnerability scanner is a thing of the past and is no longer an effective method of determining a business's true security posture. Learn effective penetration testing skills so that you can effectively meet and manage the rapidly changing security needs of your company. Advanced Penetration Testing for Highly-Secured Environments will teach you how to efficiently and effectively ensure the security posture of environments that have been secured using IDS/IPS, firewalls, network segmentation, hardened system configurations and more. The stages of a penetration test are clearly defined and addressed using step-by-step instructions that you can follow on your own virtual lab.The book follows the standard penetration testing stages from start to finish with step-by-step examples. The book thoroughly covers penetration test expectations, proper scoping and planning, as well as enumeration and footprinting. You'll learn how to clean up and compile proof of concept, exploit code from the web, advanced web application testing techniques, client side attacks, post exploitation strategies, detection avoidance methods, generation of well defined reports and metrics, and setting up a penetration testing virtual lab that mimics a secured environment. The book closes by issuing a challenge to your skills and ability to perform a full penetration test against a fictional corporation; followed by a detailed walk through of the solution.Advanced Penetration Testing for Highly-Secured Environments is packed with detailed examples that reinforce enumeration, exploitation, post-exploitation, reporting skills and more.
Table of Contents (18 chapters)
Advanced Penetration Testing for Highly-Secured Environments: The Ultimate Security Guide
About the Author
About the Reviewers


Penetration testers are faced with a combination of firewalls, intrusion detection systems, host-based protection, hardened systems, and teams of knowledgeable analysts that pour over data collected by their security information management systems. In an environment such as this, simply running automated tools will typically yield few results. The false sense of this security can easily result in the loss of critical data and resources.

Advanced Penetration Testing for Highly Secured Environments provides guidance on going beyond the basic automated scan. It will provide you with a stepping stone which can be used to take on the complex and daunting task of effectively measuring the entire attack surface of a traditionally secured environment.

Advanced Penetration Testing for Highly Secured Environments uses only freely available tools and resources to teach these concepts. One of the tools we will be using is the well-known penetration testing platform BackTrack. BackTrack's amazing team of developers continuously update the platform to provide some of the best security tools available. Most of the tools we will use for simulating a penetration test are contained on the most recent version of BackTrack.

The Penetration Testing Execution Standard (PTES),, is used as a guideline for many of our stages. Although not everything within the standard will be addressed, we will attempt to align the knowledge in this book with the basic principles of the standard when possible.

Advanced Penetration Testing for Highly Secured Environments provides step-by-step instructions on how to emulate a highly secured environment on your own equipment using VirtualBox, pfSense, snort, and similar technologies. This enables you to practice what you have learned throughout the book in a safe environment. You will also get a chance to witness what security response teams may see on their side of the penetration test while you are performing your testing!

Advanced Penetration Testing for Highly Secured Environments wraps up by presenting a challenge in which you will use your virtual lab to simulate an entire penetration test from beginning to end. Penetration testers need to be able to explain mitigation tactics with their clients; with this in mind we will be addressing various mitigation strategies that will address the attacks listed throughout the chapters.

What this book covers

Chapter 1, Planning and Scoping for a Successful Penetration Test, introduces you to the anatomy of a penetration test. You will learn how to effectively determine the scope of the penetration test as well as where to place your limits, such as when dealing with third-party vendor equipment or environments. Prioritization techniques will also be discussed.

Chapter 2, Advanced Reconnaissance Techniques, will guide you through methods of data collection that will typically avoid setting off alerts. We will focus on various reconnaissance strategies including digging into the deep web and specialty sites to find information about your target.

Chapter 3, Enumeration: Choosing Your Targets Wisely, provides a thorough description of the methods used to perform system footprinting and network enumeration. The goal is to enumerate the environment and to explain what to look for when selecting your targets. This chapter touches upon mid to advanced Nmap techniques and using PBNJ to detect changes on the network. The chapter closes with tips on how to avoid enumeration attempts as well as methods of trying to confuse an attacker (to buy time for the blue team).

Chapter 4, Remote Exploitation, will delve into the Metasploit® framework. We will also describe team based testing with Armitage. We take a look at proof of concept exploit code from which we will rewrite and compile; we also take a look at THC Hydra and John the Ripper for password attacks.

Chapter 5, Web Application Exploitation, has a focus on web application attacks. We will begin by providing step-by-step instructions on how to build a web application exploitation lab and then move toward detailing the usage of w3af and WebScarab. Load balancing is discussed in detail as many environments now have these features. We introduce you to methods of detecting web application firewalls and load balancing with hands-on examples. We finish this chapter with an introduction to the Mantra browser.

Chapter 6, Exploits and Client-Side Attacks, discusses bypassing AV signatures, details the more advanced features of the Social Engineering Toolkit, and goes over the details of buffer overflows and fuzzing.

Chapter 7, Post-Exploitation, describes the activities performed after a successful attack has been completed. We will cover privilege escalation, advanced meterpreter functionality, setting up privileged accounts on different OS types, and cleaning up afterwards to leave a pristine system behind.

Chapter 8, Bypassing Firewalls and Avoiding Detections, covers methods that can be used to attempt to bypass detection while testing. This includes avoiding intrusion detection systems and advanced evasion techniques. We also discuss methods of increasing the detectability of malicious users or applications.

Chapter 9, Data Collection Tools and Reporting, will help you create reports and statistics from all of the data that you have gathered throughout this testing. You will learn how to collect all of the testing data and how to validate results. You will also be walked through generating your report.

Chapter 10, Setting Up Virtual Testing Lab Environments, walks you through setting up a test environment that mimics a corporation that has a multitier DMZ environment using IDS and "some" hardened systems and apps. This includes setting up VBOX, BackTrack, virtual firewalls, IDS and Monitoring.

Chapter 11, Take the Challenge – Putting It All Together, will allow you to gain hands-on experience using the skills you have learned throughout the book. We will set challenges for you that require you to perform a penetration test on your testing environment from start to finish. We will offer step-by-step solutions to the challenges to ensure that the material has been fully absorbed.

What you need for this book

In order to practice the material, you will need a computer with sufficient power and space to run the virtualization tools that we need to build the lab. Any modern computer with a bit of hard drive space should suffice. The virtualization tools described within can be run on most modern Operating Systems available today.

Who this book is for

This book is for any ethical person with the drive, conviction, and the willingness to think out-of-the-box and to learn about security testing. Much of the material in this book is directed at someone who has some experience with security concepts and has a basic understanding of different operating systems. If you are a penetration tester, security consultant, or just generally have an interest in testing the security of your environment then this book is for you.

Please note:

  • The information within this book is intended to be used only in an ethical manner.

  • Do not use any of the information within this book unless you have written permission by the owner of the equipment.

  • If you perform illegal acts you should expect to be arrested and prosecuted to the full extent of the law.

  • We do not take responsibility if you misuse any of the information contained within this book.

The information herein must only be used while testing environments with proper written authorization from the appropriate persons.


In this book, you will find a number of styles of text that distinguish between different kinds of information. Here are some examples of these styles, and an explanation of their meaning.

Code words in text are shown as follows: "We will use a picture named FotoStation.jpg ".

A block of code is set as follows:

ExifTool Version Number         : 7.89
File Name                       : FlashPix.ppt
Directory                       : ./t/images
File Size                       : 9.5 kB

When we wish to draw your attention to a particular part of a code block, the relevant lines or items are set in bold:


HTTP/1.1 200 OK
Content-Length: 9908
Content-Type: text/html

Any command-line input or output is written as follows:

# cd /pentest/enumeration/google/metagoofil

New terms and important words are shown in bold. Words that you see on the screen, in menus or dialog boxes for example, appear in the text like this: "Setting the Network adapter to Internal Network allows our BackTrack system to share the same subnet with the newly-created Ubuntu machine."


Warnings or important notes appear in a box like this.


Tips and tricks appear like this.

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