Table Of ContentLearn Penetration Testing
Understand the art of penetration testing and develop your
white hat hacker skills
Rishalin Pillay
BIRMINGHAM - MUMBAI
Learn Penetration Testing
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ISBN 978-1-83864-016-3
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This book is dedicated to my best friend, my life companion, and the mother of our child -
Rubleen Pillay. Without your support, patience, and love, this book would not have been
possible. Thank you for all the long nights that you have spent with Kai while I wrote this book.
I love you, you absolutely ROCK!
– Rishalin Pillay
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Contributors
About the author
Rishalin Pillay has over 12 years' cybersecurity experience, and has acquired a vast amount
of skills consulting for Fortune 500 companies while taking part in projects performing
tasks in network security design, implementation, and vulnerability analysis.
He holds many certifications that demonstrate his knowledge and expertise in the
cybersecurity field from vendors such as ISC2, Cisco, Juniper, Checkpoint, Microsoft,
CompTIA, and more.
Rishalin currently works at a large software company as a Senior Cybersecurity Engineer.
I would like to thank Packt Publishing for giving me an opportunity to write this book. A
special thank you to Jordina D'cunha and the team for all the support they have provided
me during this journey.
About the reviewer
Chris Griffin has been involved in cybersecurity since 2002, starting in Security
Operations Centre (SOC) and internal penetration testing. In 2004, he became a volunteer
for ISECOM, helping with work on the Open Source Security Testing Methodology
Manual (OSSTMM) and teaching OSSTMM certifications. This culminated in Chris
becoming a board member at ISECOM in 2014.
Chris is a regular as various security conferences around the world—a list that is ever-
growing. He has also reviewed several books and been a contributor to the book Hacking
Linux Exposed 3rd Edition, written as an ISECOM project.
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Table of Contents
Preface 1
Section 1: The Basics
Chapter 1: Introduction to Penetration Testing 8
Technical requirements 8
What is penetration testing? 9
Stages of a penetration test 10
Pre-engagement 11
Scoping 11
Timelines 12
Dealing with third parties 12
Payment 13
Your "get out of jail free card" 13
Intelligence gathering 14
Threat modeling 14
Vulnerability analysis 15
Exploitation 15
Post-exploitation 15
Reporting 16
Executive summary 16
Technical report 17
Getting started with your lab 18
Creating virtual machines in VMware, Hyper-V, and VirtualBox 20
Microsoft Hyper-V 20
VMware 23
VirtualBox 23
Target machines 23
Metasploitable 24
Summary 25
Questions 26
Chapter 2: Getting Started with Kali Linux 27
Technical requirements 28
An introduction to Kali Linux 28
Installing and configuring Kali Linux 32
Installation 32
Installing Kali Linux on macOS 33
Installing Kali Linux using the Windows Subsystem for Linux (WSL) 38
Installing Kali Linux using VirtualBox 41
Configuring Kali Linux 42
Table of Contents
Basic commands in Kali Linux 48
Scripting in Kali Linux 49
The essential tools of Kali Linux 50
Nmap 51
Aircrack-ng 51
John the Ripper (JTR) and Hydra 52
SET 52
Burp Suite 53
Summary 53
Questions 54
Section 2: Exploitation
Chapter 3: Performing Information Gathering 56
Technical requirements 57
Passive information gathering 57
Using the internet 58
Google dorks 58
Shodan 61
Shodan scripting 62
Using Kali Linux 65
Maltego 65
Active information gathering 68
Nmap 69
Vulnerability scanning 74
OpenVAS 74
Nessus 79
Capturing traffic 86
Wireshark 86
tcpdump 91
Summary 92
Questions 92
Chapter 4: Mastering Social Engineering 93
Technical requirements 93
What is social engineering? 94
Pretexting 95
Phishing 96
Spear phishing 97
Tailgating 98
Social engineering tools 98
The social engineering toolkit (SET) 98
Gophish 100
Modlishka 101
Wifiphisher 102
Creating a social engineering campaign 103
[ ii ]
Table of Contents
Installing Modlishka 103
Executing the attack 108
Using SET to create a phishing campaign 110
Summary 112
Questions 112
Chapter 5: Diving into the Metasploit Framework 113
Technical requirements 113
Introducing Metasploit 114
Updating the Metasploit Framework 115
Linking the Metasploit Framework to a database 116
Enhancing your experience within Metasploit 120
Using Metasploit to exploit a remote target 123
Finding modules 125
Exploit-DB 125
Rapid7 exploit database 126
0day.today 128
Adding modules 128
Metasploit options, shells, and payloads 130
Options 130
Shells 131
Payloads 131
Working with MSFvenom 135
Summary 137
Questions 138
Chapter 6: Understanding Password Attacks 139
Technical requirements 139
Introduction to password attacks 140
Working with wordlists 141
Password profiling 143
Password mutation 146
Offline password attacks 148
John the Ripper 150
Hashcat 153
Online password attacks 155
Hydra 155
Medusa 157
Ncrack 159
Dumping passwords from memory 162
Summary 167
Questions 167
Chapter 7: Working with Burp Suite 168
Technical requirements 168
[ iii ]
