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Home > Security > Penetration Testing > Advanced Penetration Testing for Highly-Secured Environments, Second Edition
Advanced Penetration Testing for Highly-Secured Environments, Second Edition
Advanced Penetration Testing for Highly-Secured Environments, Second Edition

Advanced Penetration Testing for Highly-Secured Environments, Second Edition: Employ the most advanced pentesting techniques and tools to build highly-secured systems and environments , Second Edition

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Advanced Penetration Testing for Highly-Secured Environments, Second Edition

Chapter 2. Preparing a Test Environment

In this chapter, we will discuss the test environment and how we will select the chosen platform. We will discuss the following:

  • Introduction to the VMware Workstation
  • Explanation of the reasoning behind selecting the platform
  • Reviewing and implementing the design of the network
  • Developing the structure to support the course and putting everything together

In the first edition of the book, the process was to develop the range in each chapter of the book. In this second edition, the process is to develop the range, at least at the network architecture level, to support the different exercises throughout the book. We will still revisit the design, but the intent is to get the layers of defense to meet the needs of the network designs throughout the book.

Introducing VMware Workstation

The selected platform for the book is the tool from VMware, and one of the early players in the virtualization market. The VMware Workstation provides us with the capability to emulate a number of different complex architectures, and this will allow us to architect the most sophisticated of networks as we build highly secure environments, so we can test the different penetration techniques against them.

At the time of writing this book, the VMware Workstation Version 11 is the current version, and it comes with a number of different features that allow for not only the creation of the complex architectures that we require, but also the capability to clone and build groups of machines for our test environment.

Why VMware Workstation?

We will not elaborate in great detail about why the decision was made to use VMware Workstation. For an in-depth discussion as well as a comparison of a number of the different virtualization tools that are available, you can refer...

Installing VMware Workstation

To obtain the software, go to the http://www.VMware.com site and download it; you will be required to register if you have not done this before. The one good thing about registering is that they will send you discount codes, and you can potentially acquire the software for a reduced price. Once you downloaded the software, install it. The installation is simple and straightforward, so we will not cover this here.

Tip

You can use the free version of software VMware Player, but it does not provide the same capability to build complex and complete architectures; however, if you do want to use it, then you can build the layers of your architecture as independent entities with the provided switches that are available after your installation.

To access the switches for the network configuration in the VMware Workstation tool click on Edit | Virtual Network Editor | Add Network. An example of this is shown in the following image:

Installing VMware Workstation

If you click on the drop down next to...

Network design

Before we start the design of the network, we will review the existing network switches that are installed by default. When you install the VMware Workstation, there are three switches installed by default. These are the following:

  • VMnet0
  • VMnet1
  • VMnet8

VMnet0

The VMnet0 switch is the Bridged switch, and it is the one that is connected to the physical network. That is not what we normally will configure in our test architecture. This is because the connection requires that there be a connected network to obtain an IP address from, and a DHCP server available. Another reason for not using the physical connection is the fact that it is the connection to the network, and as such, we could inadvertently direct an attack into the network and this could result in us attacking someone that we do not have permission to test. Furthermore, this connection is often connected to the Internet. An example of the VMnet0 switch is shown in the following image.

VMnet0

An important thing to note from the...

Understanding the default architecture

With the default configuration of the VMware Workstation, we can create a multiple layer design. If we counted the VMnet0 switch, then we could architect three segments, but, since we have discussed the downside of doing this, we will just use the first two switches to set the initial phase of the architecture for the book. As we continue, we will add additional switches until we have the final design of the network that we wish to achieve.

Installing Kali Linux

We have a number of choices when it comes to installing Kali, and the one we select is largely a personal preference; the preferred method as a tester is to install the machine from the iso image, because that will provide you with the most control over the configuration of the machine. This method can also present challenges, but for the most part, it should not be too painful. Kali can be downloaded from http://www.kali.org, and once you are there, you have a number of options for the installation...

Creating the switches

We know that we have three switches that were created when we carried out the installation. This will allow us to create a number of different architectures, but we still need more switches for our design. The system has assigned our IP addresses for the VMnet1 and VMnet8 switches, respectively. We want to customize the switches to meet the IP addresses that we will use throughout the book. We have four subnets that we use throughout the book, and we will configure them now. This does not include the last chapter, and we will customize four switches just for that. In your VMware Workstation, click on Edit | Virtual Network Editor. This will bring up the network configuration window, and we want to configure the following:

Name

Subnet Address

VMnet1

192.168.50

VMnet2

192.168.25

VMnet3

192.168.101

VMnet4

192.168.10

VMnet5

192.168.20

VMnet6

192.168.30

VMnet7

192.168.40

VMnet8

192.168.75

This will provide us with the four subnets for the...

Introducing VMware Workstation

The selected platform for the book is the tool from VMware, and one of the early players in the virtualization market. The VMware Workstation provides us with the capability to emulate a number of different complex architectures, and this will allow us to architect the most sophisticated of networks as we build highly secure environments, so we can test the different penetration techniques against them.

At the time of writing this book, the VMware Workstation Version 11 is the current version, and it comes with a number of different features that allow for not only the creation of the complex architectures that we require, but also the capability to clone and build groups of machines for our test environment.

Why VMware Workstation?

We will not elaborate in great detail about why the decision was made to use VMware Workstation. For an in-depth discussion as well as a comparison of a number of the different virtualization tools that are available, you can refer...

Installing VMware Workstation

To obtain the software, go to the http://www.VMware.com site and download it; you will be required to register if you have not done this before. The one good thing about registering is that they will send you discount codes, and you can potentially acquire the software for a reduced price. Once you downloaded the software, install it. The installation is simple and straightforward, so we will not cover this here.

Tip

You can use the free version of software VMware Player, but it does not provide the same capability to build complex and complete architectures; however, if you do want to use it, then you can build the layers of your architecture as independent entities with the provided switches that are available after your installation.

To access the switches for the network configuration in the VMware Workstation tool click on Edit | Virtual Network Editor | Add Network. An example of this is shown in the following image:

If you click on the drop down next to the...

Left arrow icon

Page 1 of 8

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Key benefits

  • Learn how to build your own pentesting lab environment to practice advanced techniques
  • Customize your own scripts, and learn methods to exploit 32-bit and 64-bit programs
  • Explore a vast variety of stealth techniques to bypass a number of protections when penetration testing

Description

The defences continue to improve and become more and more common, but this book will provide you with a number or proven techniques to defeat the latest defences on the networks. The methods and techniques contained will provide you with a powerful arsenal of best practices to increase your penetration testing successes. The processes and methodology will provide you techniques that will enable you to be successful, and the step by step instructions of information gathering and intelligence will allow you to gather the required information on the targets you are testing. The exploitation and post-exploitation sections will supply you with the tools you would need to go as far as the scope of work will allow you. The challenges at the end of each chapter are designed to challenge you and provide real-world situations that will hone and perfect your penetration testing skills. You will start with a review of several well respected penetration testing methodologies, and following this you will learn a step-by-step methodology of professional security testing, including stealth, methods of evasion, and obfuscation to perform your tests and not be detected! The final challenge will allow you to create your own complex layered architecture with defences and protections in place, and provide the ultimate testing range for you to practice the methods shown throughout the book. The challenge is as close to an actual penetration test assignment as you can get!

Who is this book for?

This book is for anyone who wants to improve their skills in penetration testing. As it follows a step-by-step approach, anyone from a novice to an experienced security tester can learn effective techniques to deal with highly secured environments. Whether you are brand new or a seasoned expert, this book will provide you with the skills you need to successfully create, customize, and plan an advanced penetration test.

What you will learn

  • A step-by-step methodology to identify and penetrate secured environments
  • Get to know the process to test network services across enterprise architecture when defences are in place
  • Grasp different web application testing methods and how to identify web application protections that are deployed
  • Understand a variety of concepts to exploit software
  • Gain proven post-exploitation techniques to exfiltrate data from the target
  • Get to grips with various stealth techniques to remain undetected and defeat the latest defences
  • Be the first to find out the latest methods to bypass firewalls
  • Follow proven approaches to record and save the data from tests for analysis

Product Details

Country selected
Publication date, Length, Edition, Language, ISBN-13
Publication date : Mar 29, 2016
Length: 428 pages
Edition : 2nd
Language : English
ISBN-13 : 9781784392024
Vendor :
VMware
Category :
Security
Concepts :
Penetration Testing
Tools :
Kali Linux

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Product Details

Publication date : Mar 29, 2016
Length: 428 pages
Edition : 2nd
Language : English
ISBN-13 : 9781784392024
Vendor :
VMware
Category :
Security
Concepts :
Penetration Testing
Tools :
Kali Linux

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Table of Contents

13 Chapters
1. Penetration Testing Essentials Chevron down icon Chevron up icon
1. Penetration Testing Essentials
Methodology defined
Example methodologies
Abstract methodology
Summary
2. Preparing a Test Environment Chevron down icon Chevron up icon
2. Preparing a Test Environment
Introducing VMware Workstation
Installing VMware Workstation
Network design
Understanding the default architecture
Creating the switches
Putting it all together
Summary
3. Assessment Planning Chevron down icon Chevron up icon
3. Assessment Planning
Introducing advanced penetration testing
Before testing begins
Planning for action
Installing LibreOffice
Effectively managing your test results
Introduction to the Dradis framework
Summary
4. Intelligence Gathering Chevron down icon Chevron up icon
4. Intelligence Gathering
Introducing reconnaissance
DNS recon
Gathering and validating domain and IP information
Using search engines to do your job for you
Creating network baselines with scanPBNJ
Summary
5. Network Service Attacks Chevron down icon Chevron up icon
5. Network Service Attacks
Configuring and testing our lab clients
Angry IP Scanner
Nmap – getting to know you
SNMP – a goldmine of information just waiting to be discovered
Network baselines with scanPBNJ
Enumeration avoidance techniques
Reader challenge
Summary
6. Exploitation Chevron down icon Chevron up icon
6. Exploitation
Exploitation – why bother?
Manual exploitation
Getting files to and from victim machines
Passwords – something you know…
Metasploit – learn it and love it
Reader challenge
Summary
7. Web Application Attacks Chevron down icon Chevron up icon
7. Web Application Attacks
Practice makes perfect
Configuring pfSense
Detecting load balancers
Detecting web application firewalls (WAF)
Taking on Level 3 – Kioptrix
Web Application Attack and Audit framework (w3af)
Introduction to browser plugin HackBar
Reader challenge
Summary
8. Exploitation Concepts Chevron down icon Chevron up icon
8. Exploitation Concepts
Buffer overflows – a refresher
64-bit exploitation
Introducing vulnserver
Fuzzing tools included in Kali
Social Engineering Toolkit
Fast-Track
Reader challenge
Summary
9. Post-Exploitation Chevron down icon Chevron up icon
9. Post-Exploitation
Rules of Engagement
Data gathering, network analysis, and pillaging
Pivoting
Reader challenge
Summary
10. Stealth Techniques Chevron down icon Chevron up icon
10. Stealth Techniques
Lab preparation
Stealth scanning through the firewall
Now you see me, now you don't – avoiding IDS
Blending in
PfSense SSH logs
Looking at traffic patterns
Cleaning up compromised hosts
Miscellaneous evasion techniques
Reader challenge
Summary
11. Data Gathering and Reporting Chevron down icon Chevron up icon
11. Data Gathering and Reporting
Record now – sort later
Old school – the text editor method
Dradis framework for collaboration
The report
Reader challenge
Summary
12. Penetration Testing Challenge Chevron down icon Chevron up icon
12. Penetration Testing Challenge
Firewall lab setup
The scenario
The virtual lab setup
The challenge
The walkthrough
Reporting
Summary
Index Chevron down icon Chevron up icon
Index

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Customer reviews

Rating distribution
Full star icon Empty star icon Empty star icon Empty star icon Empty star icon 1
(1 Ratings)
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1 star 100%
Randal T. Rioux Jul 07, 2016
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This is the first book I've ever returned after buying and reading.It does not cover "Advanced Penetration Testing," nor does it deal in any way with "Highly-Secured Environments." It is an introduction to the business side of security testing, including permission, scope and contracts (rules of engagement). Most of the text is an explanation of how to setup VMware, pfSense, Kali, Ubuntu and other host systems used in test scenarios.The only "penetration testing" covered is through the use of popular scanning and exploitation tools such as Metasploit and nmap, both of which are given far greater detail in other publications.It felt like this book was written as a beginner's guide to getting into the field of penetration testing, but was given a new title at the last minute. For about $60, I found this book to be a completely overpriced collection of common knowledge.
Amazon Verified review Amazon

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About the authors

Left arrow icon
Profile icon Cardwell
Cardwell
Kevin Cardwell is currently working as a freelance consultant and provides consulting services for companies throughout the world, and he also works as an advisor to numerous government entities within the USA, the Middle East, Africa, Asia, and the UK. He is an instructor, technical editor, and author for computer forensics and hacking courses. He is the author of the Center for Advanced Security and Training (CAST), Advanced Network Defense, and Advanced Penetration Testing courses. He is technical editor of the Learning Tree Course Penetration Testing Techniques and Computer Forensics courses. He has presented at the Black Hat USA, Hacker Halted, ISSA, and TakeDownCon conferences as well as many others. He has chaired the Cybercrime and Cyber Defense Summit in Oman and was the executive chairman of the Oil and Gas Cyber Defense Summit. He is the author of Building Virtual Pen testing Labs for Advanced Penetration Testing, 1st Edition, Advanced Penetration Testing for Highly Secured Environments, Second Edition, and Backtrack: Testing Wireless Network Security. He holds a bachelor of science degree in computer science from National University in California and a masters degree in software engineering from the Southern Methodist University (SMU) in Texas. He developed the strategy and training development plan for the first Government CERT in the country of Oman that recently was rated as the top CERT for the Middle East. He serves as a professional training consultant to the Oman Information Technology Authority, and he developed the team to man the first Commercial Security Operations Center in the country of Oman. He has worked extensively with banks and financial institutions throughout the Middle East, Europe, and the UK in the planning of a robust and secure architecture and implementing requirements to meet compliance. He currently provides consultancy to Commercial companies, governments, federal agencies, major banks, and financial institutions throughout the globe. Some of his recent consulting projects include the Muscat Securities Market (MSM), Petroleum Development Oman, and the Central Bank of Oman. He designed and implemented the custom security baseline for the existing Oman Airport Management Company (OAMC) airports and the two new airports opening in 2016 as well as for the Oman Telephone Company. He created custom security baselines for all of the Microsoft Operating Systems, Cisco devices, as well as applications.
Read more
See other products by Cardwell
Profile icon Allen
Allen
Lee Allen is the associate director at Ohio State University. He specializes in information security, penetration testing, security research, task automation, risk management, data analysis, and 3D application development.
Read more
See other products by Allen
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  • If you experience a problem with using or installing Adobe Reader, the contact Adobe directly.
  • To view the errata for the book, see www.packtpub.com/support and view the pages for the title you have.
  • To view your account details or to download a new copy of the book go to www.packtpub.com/account
  • To contact us directly if a problem is not resolved, use www.packtpub.com/contact-us
What eBook formats do Packt support? Chevron down icon Chevron up icon

Our eBooks are currently available in a variety of formats such as PDF and ePubs. In the future, this may well change with trends and development in technology, but please note that our PDFs are not Adobe eBook Reader format, which has greater restrictions on security.

You will need to use Adobe Reader v9 or later in order to read Packt's PDF eBooks.

What are the benefits of eBooks? Chevron down icon Chevron up icon
  • You can get the information you need immediately
  • You can easily take them with you on a laptop
  • You can download them an unlimited number of times
  • You can print them out
  • They are copy-paste enabled
  • They are searchable
  • There is no password protection
  • They are lower price than print
  • They save resources and space
What is an eBook? Chevron down icon Chevron up icon

Packt eBooks are a complete electronic version of the print edition, available in PDF and ePub formats. Every piece of content down to the page numbering is the same. Because we save the costs of printing and shipping the book to you, we are able to offer eBooks at a lower cost than print editions.

When you have purchased an eBook, simply login to your account and click on the link in Your Download Area. We recommend you saving the file to your hard drive before opening it.

For optimal viewing of our eBooks, we recommend you download and install the free Adobe Reader version 9.