Penetration Testing Bootcamp

Penetration Testing Bootcamp

Quickly get up and running with pentesting techniques

Jason Beltrame

BIRMINGHAM - MUMBAI

Penetration Testing Bootcamp

Copyright © 2017 Packt Publishing

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First published: June 2017

Production reference: 1230617

Published by Packt Publishing Ltd.

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ISBN978-1-78728-874-4

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Credits

About the Author

Jason Beltrame is a Systems Engineer for Cisco, living in the Eastern Pennsylvania Area. He has worked in the Network and Security field for 18 years, with the last 2 years as a Systems Engineer, and the prior 16 years on the operational side as a Network Engineer. During that time, Jason has achieved the following certifications: CISSP, CCNP, CCNP Security, CCDP, CCSP, CISA, ITILv2, and VCP5. He is a graduate from DeSales University with a BS in Computer Science. He has a passion for security and loves learning.

In his current role at Cisco, Jason focuses on Security and Enterprise Networks, but as a generalist SE, he covers all aspects of technology. Jason works with commercial territory customers, helping them achieve their technology goals based on their individual business requirements. His 16 years of real-world experience allows him to relate with his customers and understand both their challenges and desired outcomes.

I would like to thank my wife, Becky, for her support and love, as well as everything that she does. I would also like to thank both my children, Josh and Ryan, for supporting me along the way, and helping me relax and put things in perspective. Without this strong support system that I have, none of this would have been possible. Finally, I would like to thank Mike McPhee and Joey Muniz for their support in writing this new book. ;

About the Reviewer

Kubilay Onur Gungor has been working in the Cyber Security field for more than 8 years. He started his professional career with cryptanalysis of encrypted images using chaotic logistic maps. After working as a QA tester in the Netsparker Project, he continued his career in the penetration testing field. He performed many penetration tests and consultancies on the IT infrastructure of many large clients, such as banks, government institutions, and telecommunication companies.

Following his pentesting activities, he worked as a web application security expert and incident management and response expert Sony Europe and Global Sony Electronics.

Kubilay believes in a multidisciplinary approach to cyber security and defines it as a struggle. With this approach, he has developed his own unique certification and training program, including, penetration testing-malware analysis, incident management and response, cyber terrorism, criminal profiling, unorthodox methods, perception management, and international relations. Currently, this certification program is up and running in Istanbul as cyberstruggle.org. Besides security certificates, he holds foreign policy, brand management, surviving in extreme conditions, international cyber conflicts, anti-terrorism accreditation board, terrorism and counter-terrorism comparing studies certificates.

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Table of Contents

Preface

What this book covers

What you need for this book

Who this book is for

Conventions

Reader feedback

Customer support

Errata

Piracy

Questions

Planning and Preparation

Why does penetration testing take place?

Understanding the engagement

Defining objectives with stakeholder questionnaires

Scoping criteria

Documentation

Understanding the network diagram – onshore IT example

Data flow diagram

Organization chart

Building the systems for the penetration test

Penetration system software setup

Summary

Information Gathering

Understanding the current environment

Where to look for information – checking out the toolbox!

Search engines as an information source

Utilizing whois for information gathering

Enumerating DNS with dnsmap

DNS reconnaissance with DNSRecon

Checking for a DNS BIND version

Probing the network with Nmap

Checking for DNS recursion with NSE

Fingerprinting systems with P0f

Firewall reconnaissance with Firewalk

Detecting a web application firewall

Protocol fuzzing with DotDotPwn

Using Netdiscover to find undocumented IPs

Enumerating your findings

Summary

Setting up and maintaining the Command and Control Server

Command and control servers

Setting up secure connectivity

Inside server SSH setup

Command and control server SSH setup

Setting up a reverse SSH tunnel

stunnel to the rescue

stunnel setup on the client – Raspberry Pi

Verifying automation

Automating evidence collection

File utilities

Playing with tar

Split utility

Summary

Vulnerability Scanning and Metasploit

Vulnerability scanning tools

Scanning techniques

OpenVAS

Getting started with OpenVAS

Performing scans against the environment

Getting started with Metasploit

Exploiting our targets with Metasploit

Understanding client-side attacks

Using BeEF for browser-based exploitation

Using SET for client-side exploitation

Summary

Traffic Sniffing and Spoofing

Traffic sniffing tools and techniques

Sniffing tools

Tcpdump

WinDump

Wireshark

Understanding spoofing attacks

ARP spoofing

Ettercap

SSLStrip

Intercepting SSL traffic with SSLsplit

Summary

Password-based Attacks

Generating rainbow tables and wordlists

Creating rainbows with RainbowCrack

Crunching wordlists

Online locations

Cracking utilities

John the Ripper

THC-Hydra

Ncrack

Medusa

Social engineering experiments

Impersonation to get the goods

Scenario 1

Scenario 2

Dumpster diving

Free USB drives for all!!

Summary

Attacks on the Network Infrastructure

attacks

snmp-check

Rogue DHCP server

Denial-of-service checks

Various attacks with hping3

Land attacks with hping3

Smurf attacks using hping3

MAC flooding with Macof

Wireless-based attacks

Cracking WPA2 with aircrack-ng

Monitoring the airway with Kismet

Attacking WEP with wifite

Bluetooth probing

Bluelog

Btscanner

Blueranger

Scanning with Hcitool

Physical security considerations

Secure access

Employee/vendor identification

Summary

Web Application Attacks

Manipulation by client-side testing

Cross-site scripting attacks

Reflected XSS attack

Stored XSS attack

Using OWASP ZAP to find session issues

Infrastructure and design weaknesses

Uniscan

Using Skipfish for web application recon

Identity-based testing

Role based access control

Apache-users

Wfuzz

Validating data, error handling, and logic

SQL Injection fun with Sqlmap

Error handling issues

Session management

Burp suite with intercept

Using XSS for cookie retrieval

Summary

Cleaning Up and Getting Out

Cleaning up any trails left behind

Covering your tracks

Clearev with Metasploit

Shredding files with shred

CLI tips for hiding your tracks

ClearLogs for Windows

Using DD and mkfs to clear drives

LUKS Nuke blowing up partition

Destroying equipment

Stakeholder-sponsored destruction

Destruction by the penetration tester

Summary

Writing Up the Penetration Testing Report

Gathering all your data

Importance of defining risk

Structure of a penetration test report

Cover sheet

Table of contents

Executive summary

The scope of the project

Objectives of the penetration test

Description of risk rating scale

Summary of findings

Detailed findings

Conclusion

Appendix A - tools used

Appendix B - attached reports

Appendix C attached diagrams

About your company

Building the report

Delivering the report

Summary

Preface

Penetration testing is becoming an important skill set for any individual to have within their toolset with the proliferation of security threats in today’s modern landscape. The issue at hand is that many individuals just don’t know where to start learning the proper way to run a penetration test for their organization. The focus of this book is to help individuals understand the penetration testing process as well as learn about the different aspects of the penetration test. Using a Raspberry Pi running on Kali Linux and various workstations and servers, we will go through various testing scenarios using open source tools to not only tell you how to use these tools but also show you how to interpret the results. This way, as you work your way through the book, you can apply what you learn daily to whichever penetration testing project you may be working on.

What this book covers

Chapter 1, Planning and Preparation, gets you started with the penetration testing process by using real world examples of what is required to prepare. This allows you to build the foundation of the penetration test by discussing what the goals are as well as getting buy-in from management.

Chapter 2, Information Gathering, shows the reader how to start gathering information about the environment as well as the type of information to obtain. Reconnaissance is a very important step and can make or break the penetration test.

Chapter 3, Setting up and maintaining the Command and Control Server, works with getting set up with connectivity to a C&C server that can help you with intelligence gathering and offsite processing.

Chapter 4, Vulnerability Scanning and Metasploit, focuses on scanning the environment for vulnerabilities and then using this information to try and exploit the targets that are found.

Chapter 5, Traffic Sniffing and Spoofing, gets you started on how to sniff the network and then utilize this information to run various attacks like Man-in-the-Middle attacks and spoofing attacks to gain even more insight and intelligence of what is happening on the network.

Chapter 6, Password-based Attacks, shows you the process of running various password-based attacks, obtaining credentials, and utilizing this information for future penetration testing attacks.

Chapter 7, Attacks on the Network Infrastructure, looks at the infrastructure as part of the penetration test. We will explore tools to find various holes within the infrastructure before the bad guys do.

Chapter 8, Web Application Attacks, explores how to probe and exploit web applications as part of our penetration test.

Chapter 9, Cleaning Up and Getting Out, focuses on the importance of cleaning up your tracks left behind after the penetration test is complete.

Chapter 10, Writing Up the Penetration Testing Report, the final culmination of the book, shows not only the importance of the penetration testing report but also how to format it and fill with data that was obtained during our tests.

What you need for this book

To be able to utilize the concepts and examples in this book, having a Raspberry Pi 3 with Kali Linux is definitely recommended. It is also recommended to have additional workstations/laptops available to help not only test but also process some of the more hardware intensive tools. Kali Linux is the operating system of choice as well as the other utilities/tools that are discussed in this book . These are all open source, meaning they are free to download and use. The hardware and software covered in this book are not required if you are just looking to learn about the process of penetration testing.

Who this book is for

This book is designed for anyone who wants to learn how a penetration test works. The layout of the book allows the reader to follow along with what they are learning on a chapter-by-chapter basis, and apply it to their real-life penetration tests. The great thing about the topics in this book is that even though the book is written by applying the knowledge you are learning into practical use, it is not required to use the book in that method. Just reading through the book will allow you to understand the penetration testing process from start to finish. Prior knowledge about networking and Linux would be an advantage; however, it is not required to follow the concepts covered in this book. Additionally, having a prior understanding of security and penetration tests at a base level will definitely be advantageous but not required due to lots of examples within the book.

Conventions

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

Code words in text, database table names, folder names, filenames, file extensions, pathnames, dummy URLs, user input, and Twitter handles are shown as follows: you will want to write the image to it using the dd command.

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

New terms and important words are shown in bold. Words that you see on the screen, for example, in menus or dialog boxes, appear in the text like this: You will need to go into VMware Fusion and navigate to File | New.

Warnings or important notes appear in a box like this.

Tips and tricks appear like this.

Reader feedback

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Errata

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Piracy

Piracy