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Home > Security > Penetration Testing > Penetration Testing with Raspberry Pi
Penetration Testing with Raspberry Pi
Penetration Testing with Raspberry Pi

Penetration Testing with Raspberry Pi: A portable hacking station for effective pentesting , Second Edition

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Penetration Testing with Raspberry Pi

Chapter 2.  Preparing for Battle

Despite the massive improvements the Raspberry Pi 3 makes over its predecessors, it should still be considered an underpowered platform for security assessments. That being said, it is designed as a low-cost, ultra-portable computer primarily targeting educators and hobbyists. That gives it an advantage in covert, on-site penetration testing and other discreet engagements. Our focus for this chapter will be on how to prepare a Raspberry Pi (or other platforms) running Kali Linux for the management access and connectivity it will need during all phases of a penetration test.

We'll cover the following topics in this chapter:

  • Using a Command and Control server
  • Preparing for a penetration test
  • Setting up the SSH service
  • SSH default keys and management
  • Reverse shell through SSH
  • Using stunnel and other tunneling protocols
  • Setting up Remote GUI Access
  • Overclocking
  • Setting up the wireless interface
  • Setting up the Bluetooth interface
  • Setting up a 3G USB modem...

The Command and Control server

In the first edition of the book, the Raspberry Pi B+ was used, constrained by a single core and running at much lower speeds, even with overclocking. With the Raspberry Pi 3 used in this book, we now have four cores running over 1 GHz and four times more RAM to work with, so the Pi itself can certainly handle more tools and workload. That being said, it is still advisable that we budget our resources and leverage offline computing wherever possible, as more involved penetration testing can benefit from multiple sensors (Pis) and higher powered computing to correlate data effectively. We will cover tuning filtering captured data in Chapter 5, Taking Action – Intrude and Exploit.

When planning to remotely access multiple Raspberry Pi systems, we recommend setting up a central (C&C or C2Command and Control (C&C or C2) server rather than accessing each box individually. The C&C server will probably be a more powerful system so it can focus...

Preparing for a penetration test

The Kali Linux ARM image we covered in Chapter 1, Choosing a Pen Test Platform, has already been optimized for a Raspberry Pi 2 or 3. We found however that it is recommended to perform a few additional steps to ensure we are using Kali Linux in the most stable mode to avoid crashing the Raspberry Pi. The steps are as follows:

  1. We first recommended performing the OS updates as described in detail in Chapter 1, Choosing a Pen Test Platform. We won't repeat the steps here, so if we have not updated our OS, please go back to Chapter 1, Choosing a Pen Test Platform and follow the instructions.
  2. The next step we should perform is to properly identify our Raspberry Pi. The Kali Linux image ships with a generic hostname. To change the hostname, we'll use the Linux editor of our choice (seriously, any one will do; even if we are a fan of nano - this is a judgement-free zone) to edit /etc/hostname. The only thing in this file should be our hostname. We...

Setting up the SSH service

The Secure Shell (SSH) gives us full access to the Kali Linux operating system on a Raspberry Pi from a remote location. It is the most common and secure way to manage Linux systems using a command line. Since the Kali Linux GUI is not needed for most penetration testing exercises, we recommend using SSH or command-line utilities whenever possible. We found some installations of Kali Linux have SSH enabled while others may need us to install the OpenSSH server:

  1. We need to verify whether the SSH service is installed. We can do so by typing in the service --status-all command to check whether the SSH service is running. If we see +, as shown in the following screenshot, we are good to go. If we see a - sign, then we will need to install the OpenSSH server.
  2. To install OpenSSH, we type apt-get install openssh-server:

    Setting up the SSH service

  3. Once the installation is complete, we can then ensure that it will be a persistent process, meaning that it will be enabled with all reboots. We do this...

SSH default keys and management

A major security flaw in how systems are deployed is presented by the use of default or factory-installed keys and certificates. While these sorts of flaw are a boon for us as penetration testers, we need to ensure we do not fall victim to the same exploits that our targets may fall victim to by our hand. Linux distributions (as well as most any manufactured device) use factory keys by default. We must change our own key to ensure we do not become the prey to any investigator or adversary with forensics knowledge can and will access our data to determine who planted the Raspberry Pi. Let's not make it easy for them. We can do this by backing up the old keys and then establishing new ones as follows:

  1. We'll make a new directory and then move the old keys to it for storage:
    cd /etc/ssh
mkdir backup_keys
mv ssh_host_* backup_keys
  2. Then we can generate new keys for SSH and all dependent services by typing dpkg-reconfigure openssh-server, as seen in the...

The Command and Control server

In the first edition of the book, the Raspberry Pi B+ was used, constrained by a single core and running at much lower speeds, even with overclocking. With the Raspberry Pi 3 used in this book, we now have four cores running over 1 GHz and four times more RAM to work with, so the Pi itself can certainly handle more tools and workload. That being said, it is still advisable that we budget our resources and leverage offline computing wherever possible, as more involved penetration testing can benefit from multiple sensors (Pis) and higher powered computing to correlate data effectively. We will cover tuning filtering captured data in Chapter 5, Taking Action – Intrude and Exploit.

When planning to remotely access multiple Raspberry Pi systems, we recommend setting up a central (C&C or C2Command and Control (C&C or C2) server rather than accessing each box individually. The C&C server will probably be a more powerful system so it can focus on CPU-intensive...

Preparing for a penetration test

The Kali Linux ARM image we covered in Chapter 1, Choosing a Pen Test Platform, has already been optimized for a Raspberry Pi 2 or 3. We found however that it is recommended to perform a few additional steps to ensure we are using Kali Linux in the most stable mode to avoid crashing the Raspberry Pi. The steps are as follows:

  1. We first recommended performing the OS updates as described in detail in Chapter 1, Choosing a Pen Test Platform. We won't repeat the steps here, so if we have not updated our OS, please go back to Chapter 1, Choosing a Pen Test Platform and follow the instructions.

  2. The next step we should perform is to properly identify our Raspberry Pi. The Kali Linux image ships with a generic hostname. To change the hostname, we'll use the Linux editor of our choice (seriously, any one will do; even if we are a fan of nano - this is a judgement-free zone) to edit /etc/hostname. The only thing in this file should be our hostname. We can see in our example...

Setting up the SSH service

The Secure Shell (SSH) gives us full access to the Kali Linux operating system on a Raspberry Pi from a remote location. It is the most common and secure way to manage Linux systems using a command line. Since the Kali Linux GUI is not needed for most penetration testing exercises, we recommend using SSH or command-line utilities whenever possible. We found some installations of Kali Linux have SSH enabled while others may need us to install the OpenSSH server:

  1. We need to verify whether the SSH service is installed. We can do so by typing in the service --status-all command to check whether the SSH service is running. If we see +, as shown in the following screenshot, we are good to go. If we see a - sign, then we will need to install the OpenSSH server.

  2. To install OpenSSH, we type apt-get install openssh-server:

  3. Once the installation is complete, we can then ensure that it will be a persistent process, meaning that it will be enabled with all reboots. We do this...

SSH default keys and management

A major security flaw in how systems are deployed is presented by the use of default or factory-installed keys and certificates. While these sorts of flaw are a boon for us as penetration testers, we need to ensure we do not fall victim to the same exploits that our targets may fall victim to by our hand. Linux distributions (as well as most any manufactured device) use factory keys by default. We must change our own key to ensure we do not become the prey to any investigator or adversary with forensics knowledge can and will access our data to determine who planted the Raspberry Pi. Let's not make it easy for them. We can do this by backing up the old keys and then establishing new ones as follows:

  1. We'll make a new directory and then move the old keys to it for storage:

    cd /etc/ssh
mkdir backup_keys
mv ssh_host_* backup_keys

  2. Then we can generate new keys for SSH and all dependent services by typing dpkg-reconfigure openssh-server, as seen in the following...

Reverse shell through SSH

The small form factor of the Raspberry Pi makes it an awesome platform for concealed or otherwise inconspicuous deployment inside the customer's environment. Many organizations have security measures in place to block incoming connections with the goal of preventing backdoors into their network. In a white-box assessment, we may be explicitly able to open up a Firewall to permit SSH to our Raspberry Pi, as shown in the following image. The bad news is even if this is possible from a policy standpoint, it may be difficult to achieve when dealing with multiple sites under multiple administrative controls. Either way, breaking through perimeter defenses as step 1 of a penetration test, however, makes a lot of noise and will leave us either frustrated or looking for work. So how do we, out here in the wild, communicate with our Raspberry Pi 3 on the inside?

We can take advantage of the fact that most organizations do not restrict outbound traffic by default on their...

SSL tunnelling

Many administrators will have detection technologies such as IDS/IPS to detect and prevent open VPN connections. One method we can employ to get around this is levering an SSL tunneling package or proxy. While stunnel was used in the first edition of this book, we evaluated several alternatives, such as sslh, ncat, cryptcat, hitch, ptunnel, and nginx, should stunnel fail to meet our needs. While each of these grew out of different use cases (that is, server load balancing with HAProxy), with some effort all of them can create secure communication between a TCP client and server by hiding our covert payload inside another SSL (or other benign protocol's) envelope. Each package does so by using industry-standard crypto libraries such as OpenSSL or ping. What makes these tools useful to us is that they add varying levels of privacy and functionality to commonly used daemons and services without any changes in the program's code, giving us a lot of potential applications to hide...

Using the GUI

While penetration testing can be completed through exclusive use of the CLI, the added power of the Pi 3 allows us to entertain using the X11 Windows capabilities of Kali remotely. We recommend limiting this to training and initial system configuration so as to limit the traffic to and from the Pi and avoid triggering suspicion.

With that in mind, we have two basic methods we'll cover here:

  • Our primary (and most useful method for this book) is to transport of our X-Windows sessions via SSH to our laptop/desktop from which we are commanding our attack. In using this approach, we are able to protect the session using SSH, as well as use less bandwidth because the X-windows sessions only transport the application of interest for the time needed.

  • Our secondary method is to port the entire desktop via RDP or VNC. This approach, while more welcoming to Linux learners, consumes more bandwidth and relies on the implementer (the users) to ensure security is considered.

We'll walk through...

Overclocking

Overclocking the Raspberry Pi can improve the performance, but we risk greatly reducing the life of the hardware and will certainly void any warranties we may have through our kit provider. Given that the Raspberry Pi 3 is a much more powerful platform with a 1 GHz+ quad-core processor, there is likely little reason to overclock our Raspberry Pi 3 for use in penetration testing. If we find we need more processing horsepower, we are in most cases better off using higher-powered platforms for the workload and leveraging the Raspberry Pi 3 for remote sensing and collection. Either way, we should be fully aware of this risk before proceeding.

Note that the Raspberry Pi 3 still is not officially supported for overclocking, third-party tools and procedures (search engines can be a huge help here) such as those provided at http://www.jackenhack.com/raspberry-pi-3-overclocking/ will be needed to run at higher clock speeds.

Note

Overclocking will require more power from the Raspberry Pi...

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Key benefits

  • Quickly turn your Raspberry Pi 3 into a low-cost hacking tool using Kali Linux 2
  • Protect your confidential data by deftly preventing various network security attacks
  • Use Raspberry Pi 3 as honeypots to warn you that hackers are on your wire

Description

This book will show you how to utilize the latest credit card sized Raspberry Pi 3 and create a portable, low-cost hacking tool using Kali Linux 2. You’ll begin by installing and tuning Kali Linux 2 on Raspberry Pi 3 and then get started with penetration testing. You will be exposed to various network security scenarios such as wireless security, scanning network packets in order to detect any issues in the network, and capturing sensitive data. You will also learn how to plan and perform various attacks such as man-in-the-middle, password cracking, bypassing SSL encryption, compromising systems using various toolkits, and many more. Finally, you’ll see how to bypass security defenses and avoid detection, turn your Pi 3 into a honeypot, and develop a command and control system to manage a remotely-placed Raspberry Pi 3. By the end of this book you will be able to turn Raspberry Pi 3 into a hacking arsenal to leverage the most popular open source toolkit, Kali Linux 2.0.

Who is this book for?

If you are a computer enthusiast who wants to learn advanced hacking techniques using the Raspberry Pi 3 as your pentesting toolbox, then this book is for you. Prior knowledge of networking and Linux would be an advantage.

What you will learn

  • * Install and tune Kali Linux 2 on a Raspberry Pi 3 for hacking
  • * Learn how to store and offload pentest data from the Raspberry Pi 3
  • * Plan and perform man-in-the-middle attacks and bypass advanced encryption techniques
  • * Compromise systems using various exploits and tools using Kali Linux 2
  • * Bypass security defenses and remove data off a target network
  • * Develop a command and control system to manage remotely placed Raspberry Pis
  • * Turn a Raspberry Pi 3 into a honeypot to capture sensitive information
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Publication date, Length, Edition, Language, ISBN-13
Publication date : Nov 30, 2016
Length: 316 pages
Edition : 2nd
Language : English
ISBN-13 : 9781787126138
Category :
Security
Concepts :
Penetration Testing
Tools :
Kali Linux

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Product Details

Publication date : Nov 30, 2016
Length: 316 pages
Edition : 2nd
Language : English
ISBN-13 : 9781787126138
Category :
Security
Concepts :
Penetration Testing
Tools :
Kali Linux

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Table of Contents

7 Chapters
1. Choosing a Pen Test Platform Chevron down icon Chevron up icon
1. Choosing a Pen Test Platform
Hardware options and why the Pi
Software option and why Kali
Purchasing a Raspberry Pi
Assembling a Raspberry Pi
Installing Kali Linux
Combining Kali Linux and the Raspberry Pi
Cloning the Raspberry Pi SD card
Avoiding common problems
Summary
2. Preparing for Battle Chevron down icon Chevron up icon
2. Preparing for Battle
The Command and Control server
Preparing for a penetration test
Setting up the SSH service
SSH default keys and management
Reverse shell through SSH
SSL tunnelling
Using the GUI
Overclocking
Setting up the wireless interface
Setting up the Bluetooth interface
Setting up a 3G or 4G modem
Wrapping it up with an example
3. Planning the Attack Chevron down icon Chevron up icon
3. Planning the Attack
Understanding the Cyber or Intrusion Kill Chain
Preparing for the penetration test
Common tools for web, wired, and wireless attacks
Mapping our tools to the Penetration test Kill Chain
Summary
4. Explore the Target - Recon and Weaponize Chevron down icon Chevron up icon
4. Explore the Target - Recon and Weaponize
Prospecting the target
Network scanning
Seeing and cracking Wi-Fi
Capturing and cracking passwords
Getting data to the Pi
Wireshark
dsniff
Firewalk
Web application hacks
Driftnet
Summary
5. Taking Action - Intrude and Exploit Chevron down icon Chevron up icon
5. Taking Action - Intrude and Exploit
Using the Metasploit framework to exploit targets
Social engineering
Executing man-in-the-middle attacks
Rogue Access honeypot (revising and re-shooting)
Bluetooth testing
Summary
6. Finishing the Attack - Report and Withdraw Chevron down icon Chevron up icon
6. Finishing the Attack - Report and Withdraw
Covering our tracks
Masking our network footprint
Developing reports
Moving data
Summary
7. Alternative Pi Projects Chevron down icon Chevron up icon
7. Alternative Pi Projects
Diving into PwnPi
Discovering Raspberry Pwn
Investigating PwnBerry Pi
Defending your network
Running Raspberry Pi on your PC with QEMU emulator
Running Windows 10 on Raspberry Pi 3
Other popular use cases for the Raspberry Pi
Summary

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Customer reviews

Rating distribution
Full star icon Full star icon Full star icon Full star icon Half star icon 4.3
(4 Ratings)
5 star 50%
4 star 25%
3 star 25%
2 star 0%
1 star 0%
Berlinerk Apr 11, 2019
Full star icon Full star icon Full star icon Full star icon Full star icon 5
Lots of great information about more ways to use the pi!!!!!
Amazon Verified review Amazon
Amazon Customer Nov 30, 2017
Full star icon Full star icon Full star icon Full star icon Full star icon 5
I'm a network geek who does routing and large scale design. Security is not a strong suit for me, and certainly not a detailed topic like pen testing. I thoroughly enjoyed reading this book and following along. I really like the discussion around kill chains and the theory behind how real-life security is supposed to work. The book is best used as a "follow along" guide with your own kit; the authors make no assumptions about the reader's ability to assemble a kit, so they provide many cost-effective options for getting started. In a world of faux security blogs and cookie cutter "experts", it is very refreshing to get practical, relevant, and modern tips from two strong players.
Amazon Verified review Amazon
JJ May 29, 2017
Full star icon Full star icon Full star icon Full star icon Empty star icon 4
OK
Amazon Verified review Amazon
Peter Sep 17, 2020
Full star icon Full star icon Full star icon Empty star icon Empty star icon 3
Complete noob to kali <me> - I have enjoyed the book thus far. I did have a few challenges with it because of outdated software. Following the book is fairly easy but frustrating when you're trying to enter commands that have been changed or replaced somehow. That's ok though, little leg work never hurt anybody. I guess it's expected at the rate tech evolves.For the most part there is alot of useful knowledge to be learned from the book and not a bad place to start for a noob.
Amazon Verified review Amazon

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$54.99
$54.99
$57.99
Learn Computer Forensics – 2nd edition
Learn Computer Forensics – 2nd edition
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Jul 2022 434 pages
Full star icon 4.9 (62)
eBook
eBook
  • eBook eBook $35.99
  • Paperback Paperback $49.99
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$35.99 $39.99
$49.99
$46.99
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About the authors

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Profile icon Jason Beltrame
Jason Beltrame
Jason Beltrame is a Systems Engineer for Cisco, living in the Eastern Pennsylvania Area. He has worked in the Network and Security field for 18 years, with the last 2 years as a Systems Engineer, and the prior 16 years on the operational side as a Network Engineer. During that time, Jason has achieved the following certifications: CISSP, CCNP, CCNP Security, CCDP, CCSP, CISA, ITILv2, and VCP5. He is a graduate from DeSales University with a BS in Computer Science. He has a passion for security and loves learning. In his current role at Cisco, Jason focuses on Security and Enterprise Networks, but as a generalist SE, he covers all aspects of technology. Jason works with commercial territory customers, helping them achieve their technology goals based on their individual business requirements. His 16 years of real-world experience allows him to relate with his customers and understand both their challenges and desired outcomes.
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Profile icon McPhee
McPhee
Michael McPhee is a systems engineer at Cisco in New York, where he has worked for the last 4 years and has focused on cyber security, switching, and routing. Mikes current role sees him consulting on security and network infrastructures, and he frequently runs clinics and delivers training to help get his customers up to speed. Suffering from a learning addiction, Mike has obtained the following certifications along the way: CEH, CCIE R&S, CCIE Security, CCIP, CCDP, ITILv3, and the Cisco Security White Belt. He is currently working on his VCP6-DV certification, following his kids to soccer games and tournaments, traveling with his wife and kids to as many places as possible, and scouting out his future all-grain beer home brewing rig. He also spends considerable time breaking his home network (for science!), much to the family's dismay. Prior to joining Cisco, Mike spent 6 years in the U.S. Navy and another 10 working on communications systems as a systems engineer and architect for defense contractors, where he helped propose, design, and develop secure command and control networks and electronic warfare systems for the US DoD and NATO allies. Prior publication: Penetration Testing with the Raspberry Pi Second Edition (with Jason Beltrame), Packt Publishing, November 2016.
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Shipping Details

USA:

'

Economy: Delivery to most addresses in the US within 10-15 business days

Premium: Trackable Delivery to most addresses in the US within 3-8 business days

UK:

Economy: Delivery to most addresses in the U.K. within 7-9 business days.
Shipments are not trackable

Premium: Trackable delivery to most addresses in the U.K. within 3-4 business days!
Add one extra business day for deliveries to Northern Ireland and Scottish Highlands and islands

EU:

Premium: Trackable delivery to most EU destinations within 4-9 business days.

Australia:

Economy: Can deliver to P. O. Boxes and private residences.
Trackable service with delivery to addresses in Australia only.
Delivery time ranges from 7-9 business days for VIC and 8-10 business days for Interstate metro
Delivery time is up to 15 business days for remote areas of WA, NT & QLD.

Premium: Delivery to addresses in Australia only
Trackable delivery to most P. O. Boxes and private residences in Australia within 4-5 days based on the distance to a destination following dispatch.

India:

Premium: Delivery to most Indian addresses within 5-6 business days

Rest of the World:

Premium: Countries in the American continent: Trackable delivery to most countries within 4-7 business days

Asia:

Premium: Delivery to most Asian addresses within 5-9 business days

Disclaimer:
All orders received before 5 PM U.K time would start printing from the next business day. So the estimated delivery times start from the next day as well. Orders received after 5 PM U.K time (in our internal systems) on a business day or anytime on the weekend will begin printing the second to next business day. For example, an order placed at 11 AM today will begin printing tomorrow, whereas an order placed at 9 PM tonight will begin printing the day after tomorrow.


Unfortunately, due to several restrictions, we are unable to ship to the following countries:

  1. Afghanistan
  2. American Samoa
  3. Belarus
  4. Brunei Darussalam
  5. Central African Republic
  6. The Democratic Republic of Congo
  7. Eritrea
  8. Guinea-bissau
  9. Iran
  10. Lebanon
  11. Libiya Arab Jamahriya
  12. Somalia
  13. Sudan
  14. Russian Federation
  15. Syrian Arab Republic
  16. Ukraine
  17. Venezuela
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