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 Implementing
Cryptography Using
Python®
Shannon W. Bray
Published by
John Wiley & Sons, Inc.
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Copyright © 2020 by John Wiley & Sons, Inc., Indianapolis, Indiana

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 To Stephanie, Eden, Hayden, and Kenna,
with all my love, for making each and every day special.
 About the Author

Shannon W. Bray started his career in information technology in 1997 after

being honorably discharged from the United States Navy. He started his IT
career working on programmable logic controllers out in the Gulf of Mexico
and then started writing business applications using various technologies until
2000 when .NET was first released; since then, the languages of choice have
been C++, C#, Windows PowerShell, and Python. From there, Shannon worked
on writing software until he started working with Microsoft SharePoint. The
Microsoft stack of technologies forced Shannon out of just writing code into
building large secure solutions. Shannon’s career has taken him to engagements
all over the world where he has worked with a number of U.S. government
agencies. Shannon became interested in cryptography while pursuing a master’s
degree in cybersecurity, and he has continued to research cryptography and
cybersecurity as he pursues a PhD in computer science.
Shannon has earned the following certifications: Microsoft Certified Master,
Microsoft Certified Solutions Master, Certified Information Security Manager
(CISM), Security+ (Plus), the CompTIA Advanced Security Practitioner (CASP+),
and a number of other industry certifications. In addition to writing, Shannon
speaks nationally at technology conventions and works as a mentor teaching
technology to youth programs.
Shannon lives in the Raleigh, North Carolina, area with his wife, Stephanie,
two daughters, Eden and Kenna, and son, Hayden. During the dive season,
Shannon enjoys diving off the coast of North Carolina. During the rest of the
year, Shannon works on IT projects around the house that utilize single-board
computers and, most often, propellers. He is currently building a home security
system that uses Python, cryptography, and drones. As of the release of this

v
vi About the Author

book, Shannon is currently running for the U.S. Senate for the state of North
Carolina to help bring cybersecurity issues to the mainstream and to help people
understand the importance of end-to-end encryption.
Shannon can be contacted through LinkedIn at www.linkedin.com/in/
shannonbray.
 Acknowledgments

While this is my third book, every book comes with its own set of challenges.
Completing a book is not always a fun project but does become a labor of love.
As soon as you start, life has a way of throwing changes at you, and it seems
that you never have the time that you thought you would have. Shortly after
starting this book, I started a PhD program with the Missouri University of
Science and Technology and transitioned through a number of government
contracts, ran for political office, and then became a work-from-home teacher
as the world battled a global pandemic. I knew that the editing team would be
earning their pay with whatever I put together. That team has been wonderful
with their feedback and responsiveness. Specifically, I’d like to thank the follow-
ing people on the Wiley team: Barath Kumar Rajasekaran, production editor;
Jim Minatel, acquisitions editor; Pete Gaughan, content enablement manager;
Brent Cook and James Langbridge, technical editors, and, most importantly,
Kim Wimpsett, the project editor. Kim did her best to keep me on schedule, but
I found new ways to miss a few deadlines.

vii
 Contents at a Glance

Introductionxvii
Chapter 1 Introduction to Cryptography and Python 1
Chapter 2 Cryptographic Protocols and Perfect Secrecy 31
Chapter 3 Classical Cryptography 65
Chapter 4 Cryptographic Math and Frequency Analysis 95
Chapter 5 Stream Ciphers and Block Ciphers 139
Chapter 6 Using Cryptography with Images 171
Chapter 7 Message Integrity 199
Chapter 8 Cryptographic Applications and PKI 223
Chapter 9 Mastering Cryptography Using Python 247
Index277

ix
 Contents

Introductionxvii
Chapter 1 Introduction to Cryptography and Python 1
Exploring Algorithms 2
Why Use Python? 2
Downloading and Installing Python 3
Installing on Ubuntu 4
Installing on macOS 4
Installing on Windows 4
Installing on a Chromebook 4
Installing Additional Packages 5
Installing Pip, NumPy, and Matplotlib 6
Installing the Cryptography Package 7
Installing Additional Packages 8
Testing Your Install 9
Diving into Python Basics 9
Using Variables 10
Using Strings 11
Introducing Operators 11
Understanding Arithmetic Operators 11
Understanding Comparison Operators 13
Understanding Logical Operators 13
Understanding Assignment Operators 14
Understanding Bitwise Operators 15
Understanding Membership Operators 15
Understanding Identity Operators 16

xi
xii Contents

Using Conditionals 16
Using Loops 17
for17
while18
continue18
break18
else18
Using Files 19
Understanding Python Semantics 20
Sequence Types 20
Introducing Custom Functions 26
Downloading Files Using Python 27
Introducing Python Modules 28
Creating a Reverse Cipher 29
Summary30
Chapter 2 Cryptographic Protocols and Perfect Secrecy 31
The Study of Cryptology 32
Understanding Cryptography 32
Cryptography’s Famous Family: Alice and Bob 33
Diffie-Hellman34
Data Origin Authentication 34
Entity Authentication 35
Symmetric Algorithms 36
Asymmetric Algorithms 36
The Needham-Schroeder Protocols 36
The Otway-Rees Protocol 38
Kerberos39
Multiple-Domain Kerberos 40
X.50941
Formal Validation of Cryptographic Protocols 46
Configuring Your First Cryptographic Library 47
Understanding Cryptanalysis 47
Brute-Force Attacks 47
Side-Channel Attacks 48
Social Engineering 48
Analytical Attacks 48
Frequency Analysis 48
Attack Models 49
Shannon’s Theorem 50
One-Time Pad 51
XOR, AND, and OR 51
One-Time Pad Function 56
One-Way Hashes 58
 Contents xiii

Cryptographic One-Way Hashes 59

Message Authentication Codes 60
Perfect Forward Secrecy 60
Published and Proprietary Encryption Algorithms 61
Summary62
References62
Chapter 3 Classical Cryptography 65
Password Best Practices 66
Password Storage 66
Hashing Passwords 67
Salting Passwords 67
Stretching Passwords 68
Password Tools 68
Obfuscating Data 69
ASCII Encoding 70
Base64 Encoding Text 70
Binary Data 72
Decoding72
Historical Ciphers 72
Scytale of Sparta 73
Substitution Ciphers 73
Caesar Cipher 74
ROT-1376
Atbash Cipher 77
Vigenère Cipher 77
Playfair79
Hill 2x2 83
Column Transposition 87
Affine Cipher 90
Summary93
Chapter 4 Cryptographic Math and Frequency Analysis 95
Modular Arithmetic and the Greatest Common Devisor 96
Prime Numbers 97
Prime Number Theorem 98
School Primality Test 98
Fermat’s Little Theorem 100
Miller-Rabin Primality Test 100
Generate Large Prime Numbers 104
Basic Group Theory 106
Orders of Elements 107
Modular Inverses 109
Fermat’s Little Theorem to Find the Inverse 110
Extending the GCD 111
Euler’s Theorem 111
xiv Contents

Pseudorandomness115
Breaking C’s rand() Function 116
Solving Systems of Linear Equations 117
Frequency Analysis 120
Cryptanalysis with Python 123
Using an Online Word List 125
Determining the Frequency 126
Breaking the Vigenère Cipher 129
Summary138
Chapter 5 Stream Ciphers and Block Ciphers 139
Convert between Hexdigest and Plaintext 140
Use Stream Ciphers 141
ARC4147
Vernam Cipher 148
Salsa20 Cipher 149
ChaCha Cipher 151
Use Block Ciphers 156
Block Modes of Operations 158
ECB Mode 158
CBC Mode 159
CFB Mode 160
OFB Mode 162
CTR Mode 163
Tricks with Stream Modes 164
DIY Block Cipher Using Feistel Networks 165
Advanced Encryption Standard (AES) 167
Using AES with Python 167
File Encryption Using AES 169
File Decryption Using AES 169
Summary169
Chapter 6 Using Cryptography with Images 171
Simple Image Cryptography 171
Images and Cryptography Libraries 174
Understanding the Cryptography Library 174
Understanding the Cryptosteganography Library 175
Image Cryptography 175
File Cryptography Using Fernet 176
Image Cryptography Using Fernet 179
AES and Block Modes of Operations 180
Exploring a Simple ECB Mode Example 181
Exploring a Simple CBC Mode Example 185
Applying the Examples 186
Steganography187
Storing a Message Inside an Image 188
 Contents xv

Storing a Binary File Inside an Image 192

Working with large images 195
Summary197
Chapter 7 Message Integrity 199
Message Authentication Codes 200
Hash-based Message Authentication Code 201
Using HMAC to Sign Message 202
Message Digest with SHA 203
Binary Digests 204
NIST Compliance 205
CBC-MAC206
Birthday Attacks 207
Crafting Forgeries 209
The Length Extension Attack 209
Setting Up a Secure Channel 210
Communication Channels 211
Sending Secure Messages over IP Networks 212
Create a Server Socket 212
Create a Client Socket 213
Create a Threaded Server with TCP 214
Adding Symmetric Encryption 215
Concatenate Message and MAC 218
Summary221
References222
Chapter 8 Cryptographic Applications and PKI 223
The Public-Key Transformation 224
Exploring the Basics of RSA 226
Generating RSA Certificates 229
Constructing Simple Text Encryption and
Decryption with RSA Certificates 231
Constructing BLOB Encryption and
Decryption with RSA Certificates 232
The El-Gamal Cryptosystem 235
Elliptic Curve Cryptography 238
Generating ECC Keys 240
Key Lengths and Curves 241
Diffie-Hellman Key Exchange 242
Summary245
Chapter 9 Mastering Cryptography Using Python 247
Constructing a Plaintext Communications Application 248
Creating a Server 248
Creating the Client 250
Creating the Helper File 251
Execution252
xvi Contents

Installing and Testing Wireshark 253

Implementing PKI in the Application Using RSA Certificates 255
Modifying the Server 256
Modifying the Client 257
Modifying the Helper File 258
Execution259
Implementing Diffie-Hellman Key Exchange 261
Modifying the Server File 262
Modifying the Client File 264
Modifying the Helper File 266
Creating the Diffie-Hellman Class File 270
Execution275
Wrapping Up 276
Index277
 Introduction

I initiated my journey into cryptography while studying for my undergrad. Most

of the cryptography concepts I learned were based on what one would need for
their CISSP or Security+ exams. Most of my understanding was at a high level,
and it was difficult to remember the more intricate aspects until cryptography
became a primary focus.
It wasn’t until I started my master’s in cybersecurity that I began applying
cryptographic features within a scripting environment. The concepts in this
book will help you advance your knowledge and experience as you dig deeper
into understanding the use of cryptography in Python.
Over the past few years, several governments have discussed legislation that
will ensure that any form of communication, whether it’s an email, text message, or
video chat, can always be read by the police or intelligence services if they have a
warrant. Governments are putting pressure on technology companies to give them
backdoor access or the keys to the kingdom so that they can keep the country safe.
The fight between lawmakers and encrypted messaging platforms has entered
new territory. Imagine a world where the government has seized the oppor-
tunity to scan every electronic message by government-approved scanning
software. The privacy and security of all users will suffer if law enforcement
agencies achieve their dream of breaking cryptosystems. Proponents of end-to-
end encryption, like Microsoft, Facebook, and Google, may lose their campaign
to maintain user security as a priority.
We have all heard of times when it would be beneficial for encrypted data
to magically become readable; this is often related to criminal cases. Should
criminals be allowed to plot their plans in secret? Where does the right to our
privacy start? In reality, there are technical and legal issues with allowing gov-
ernments to do this; this of course will be strongly opposed by technology and

xvii
xviii Introduction

privacy advocates. The world is at war on what can be encrypted, what should be
encrypted, and who should have the keys to unlock someone else’s encryption.
Whether you agree or disagree with what powers a nation-state should have
over encrypted communications in their country, you should understand what
encryption is, how to apply it when needed, and how to ensure that the data
you are receiving is authentic and confidential. Over the course of this book,
you will get a basic understanding of how to cryptographically secure your
messages, files, or Internet traffic using easy-to-understand Python recipes that
have been created or updated to support Python 3.

What This Book Covers

This book focuses on helping you pick the right Python environment for your
needs so that you can hit the ground running. You will get an understanding
of what algorithms are and explore the basics of Python.
Once you have an idea of where you are starting from, you will get an over-
view of what cryptography is, what perfect secrecy means, and the history of
cryptography and how its use changed our world.
To get a full understanding of some of the cryptographic concepts, a little
math is needed. You will get an understanding of how prime numbers, basic
group theory, and pseudorandom number generators help build cryptographic
solutions. This will build the foundation for understanding various stream and
block ciphers and highlight some of their encryption modes and weaknesses.
Every cryptographic discussion is better with pictures, so we will spend a
chapter focusing on how image cryptography and steganography work. We’ll also
highlight a few issues that you will need to be aware of while dealing with images.
Message integrity is just as important as message secrecy. Knowing who sent
the message to you directly relates to whether the message is credible. You will
learn how to generate message authentication codes to ensure integrity during
transit.
The strength of encryption will be shown at the end of the book when you
will learn about PKI schemes and explore how to implement elliptic curve cryp-
tography in an application. The application you build will exchange data in a
highly secure format over an unsecure channel, thus ensuring that you are able
to control your own end-to-end encryption scheme that no one will be able to
decrypt without the keys you create. I hope you find the journey as fun as I did.
 Introduction xix

What You Need to Know

This book assumes that you are fairly new to cryptography. While there is a
brief introduction to how to set up and use Python, you will get the most out of
the book if you have experience in another programming or scripting language.

What You Need to Have

The concepts presented in this book can be executed on Microsoft Windows,
Linux, Chromebook, or iOS. Your choice of editor will most likely depend on
the underlying operating system, although most of the Python recipes presented
here will execute in online editors as well as most shells that are using a Python
interpreter that is 3.0 or greater.

How to Use This Book

The topics in this book get more advanced as you progress through it, so you
can work through the material from front to back and build your skills as you
go. You can also use this book as a reference that you can consult when you
need help with the following situations:
■■ You’re stuck while trying to figure out how to secure your data.
■■ You need to do something using cryptography that you’ve never
done before.
■■ You have some time on your hands, and you’re interested in learning
something new about Python and cryptography.
The index is comprehensive, and each chapter typically focuses on a single
broad topic. Don’t be discouraged if some of the material is over your head.
As you work through the coding samples and build out the final solution, the
concepts should become easier to understand.

What’s on the Website

Nearly everything discussed in this book has examples with it. You can (and
should) download the many useful examples included with this book. We have
verified that each file will run in environments that are Python version 3.0 and
higher.
The files are located at github.com/braycrypto/cryptography, as well as at
www.wiley.com/go/cryptographywithpython.
 CHAPTER

1
Introduction to Cryptography
and Python

Cryptography is one of the most important tools we have at our disposal as

information security professionals. It provides us with the ability to protect
sensitive information from unauthorized disclosure through encryption. Cryp-
tography is the use of mathematical algorithms that can be used to transform
data either into an encrypted form (ciphertext) or into its decrypted form (plain-
text). The purpose of these algorithms can be quite complicated. The goal of this
book is to help simplify the use of cryptography using the available libraries
in Python, so you will begin your journey into cryptography by setting up a
Python environment. You’ll also get a review of using Python, and then you’ll
write your first cipher using Python. Specifically, you’ll do the following:
■■ Gain an understanding of algorithms
■■ Explore various Python installations
■■ Set up Python 3 on various machines
■■ Explore the basics of the Python language
■■ Write your first cipher using Python

1
2 Chapter 1 ■ Introduction to Cryptography and Python

Exploring Algorithms
The algorithms you will explore in this book can be quite sophisticated, but
most of the logic is encapsulated into little black boxes that allow you to inter-
face with the algorithms using functions. In the programming or mathematical
world, a function is merely a way to enter values and receive output. When using
algorithms in cryptography, we generally have two inputs for encryption and
two inputs for decryption:
■■ The encryption process will take the plaintext message (P) along with an
encryption key (K) and then run the plaintext through encryption algo-
rithms, which will return ciphertext (C).
■■ On the decryption side, the ciphertext (C) will be supplied along with the
encryption key (K), which will produce the plaintext (P) message.
As you study various encryption themes throughout this book, you will find
that they are described by three algorithms: GEN for key generation, ENC for
the encryption algorithm, and DEC for the decryption algorithm. You’ll revisit
this concept at the end of this chapter when you learn how to create a Python
function.

Why Use Python?

Using Python for cryptography is simpler than using languages such as C or
C++; while free libraries such as OpenSSL are available, their use can be quite
complex. Python removes these complexities with many built-in libraries that
aid in cryptography scripting. It is also a great choice because Python is free in
terms of license. Python can be described as an open-source, general-purpose
language that is object oriented, functional, and procedural, and it allows for
the interface with C/ObjC/Java/Fortran and even .NET. A number of versions
are available, from 2.5.x through 3.x. Currently, 3.x is becoming more popular
as new libraries are introduced. Python comes preinstalled with Linux and
macOS, and you can install it on Windows as well. You will learn how to install
Python in each of these environments later in this chapter.
Because Python is available for Windows, Linux/Unix, Mac, and Chrome-
books, among others, the lessons you learn here will be portable to several
environments. Python has proven to be quite powerful in information security
and can be used to quickly script solutions to help you become a better secu-
rity practitioner. If you are using Ubuntu Linux, every command you see in
 Chapter 1 ■ Introduction to Cryptography and Python 3

this book will work. If you are on a Mac, you can use the Terminal app found
inside the Utilities folder. On a Windows machine, you have several options
as well: you can install a number of tools such as Cygwin, Visual Studio, or
PyCharm; use the Windows 10 Linux subsystem; or just install Ubuntu Linux
from the Microsoft Store. If you are new to Linux, I recommend practicing your
command-line skills a bit to help get you comfortable.
When you start the Python shell (by typing python or python3 at the command
line), you will see the version and the date associated with the version. For in-
stance, if you install and run Python in a Linux environment, you should see
something similar to the following:
Python 3.7.4+ (default, Sep 4 2019, 08:03:05)
[GCC 9.2.1 20190827] on linux
Type "help", "copyright", "credits" or "license" for more information.
>>>

The majority of Python interpreters use >>> as a prompt to accept user input;
one notable exception is IPython, which is discussed briefly in a moment. Once
you are in a Python shell, exit by pressing CTRL+D or typing exit(). Python
files use a .py extension, and we start their execution in Linux environments
by typing python3 filename.py; (keep in mind that you still need to chmod
+x the file).

N OT E In Unix-like operating systems, the chmod command sets the permissions

of files or directories.

As you will learn later in this chapter, a large number of modules are avail-
able for Python, many of which we will use along your journey of learning
cryptography. One of the more notable modules you will learn more about is
NumPy. NumPy offers numerical operations to Python, including fast multi-
dimensional array operations, random number generation, and linear algebra.
Another module that you will be introduced to is Matplotlib, which is an excel-
lent library for plotting. In Chapter 6, you will learn more about PyFITS, which
is a module that provides access to Flexible Image Transport System (FITS) files.
FITS is a portable file standard that is widely used throughout the astronomy
community to store images and tables. We will be combining it with our cryp-
tography techniques to encrypt and decrypt image files.

Downloading and Installing Python

You can download the Python interpreter from www.python.org/python, where
you’ll find versions for Ubuntu, macOS, and Windows. Be sure to download
version 3.7 or higher, since Python 2 is now unsupported.
4 Chapter 1 ■ Introduction to Cryptography and Python

Installing on Ubuntu
If you are running Ubuntu, install Python from the Ubuntu Software Center
using these steps:
1. Open the Ubuntu Software Center.
2. In the search box in the top-right corner of the window, type Python.
3. Select IDLE.
4. Click Install.

Installing on macOS
If you are using macOS, download the .dmg file for your version of macOS and
execute it. When the DMG package opens, do the following:
1. Double-click the Python package file (.mpkg).
2. Click Continue through the Welcome section and click Agree to accept
the license.
3. Select HD Macintosh and click Install.

Installing on Windows
If you are using Windows, download and run the Python installer; it should
have an .msi extension. Then follow these steps:
1. Click Install Now to begin the installation.
2. When the installation completes, click Close.
Notice the mention of upgrading. You can upgrade a package by clearing out
the Search PyPI and Installed Packages search box. This will show you all of
the installed packages. Any package that has an update will have an up arrow
next to it along with the newer version number (see Figure 1.1). You may have
to elevate your privileges.

Installing on a Chromebook
New Windows and Chrome OS computers give you the ability to install Linux.
The Chrome OS, which is becoming more popular, enables you to install a Linux
container that you can interact with but also keeps the rest of the environment
isolated so that you do not have to worry about messing up your system.
 Chapter 1 ■ Introduction to Cryptography and Python 5

Figure 1.1: Upgrading packages

To get started with Python 3 on a Chromebook, click the time in the lower-
right corner. If you have the appropriate permissions on the Chromebook, you
should see a Settings button that looks like a flower with a dot in the middle
of it. Once you are in Settings, you can scroll down until you find Linux (Beta)
and then enable it by clicking Turn On. It may take several minutes, but once
it is complete, you will be able to run Linux tools, editors, and IDEs on your
Chromebook. To continue with the Chromebook installation, see the next sec-
tion for instructions on how to install NumPy and Matplotlib.

Installing Additional Packages

Many of the coding recipes that you will find in this book require additional
packages or modules to help reduce the amount of code you need to write to
ensure message security. Most Python interpreters use a command-line approach
of loading the packages. Integrated development environments (IDEs) may have
unique ways of loading packages for each interpreter available.
6 Chapter 1 ■ Introduction to Cryptography and Python

Installing Pip, NumPy, and Matplotlib

Ensure you are in a command shell environment with a prompt. In the follow-
ing example installation, you will get an update to the packages that come with
your Python version.
Pip, or Pip3 in this case, is the package management system for Python; it is
used to install and manage software packages written in Python. Pip is similar
to tools like Bundle, NPM, and Composer in other programming languages.
NumPy, which stands for Numerical Python, is a Python package that is the
core library for scientific computing. It contains a powerful n-dimensional array
object, and provides tools for integrating C, C++, and many other languages.
Matplotlib is an excellent solution for scientific plotting; it has the ability to be
automated and produce a wide variety of customizable high-quality plots.
Once the shell is open, type the following commands:
~$ sudo apt-get update
~$ sudo apt install python-pip
~$ pip3 install numpy
~$ pip3 install matplotlib

~$ $ python3 -c "import numpy as np; import matplotlib.pyplot as plt; x

= np.linspace(0, 2 * np.pi); y = np.sin(x); plt.plot(x, y); plt.show()"

N OT E Depending on your environment, you may need to install python3-pip to

get Pip3 to work. On installs such as Ubuntu 16.04 on Windows, you will not be able to
install version 3 when you install python-pip.

To start the Python 3 shell, type the following:

~$ python3

You should see something similar to the following depending on the version
that is installed:
Python 3.X.X (default, date)
[GCC 6.3.0 20170516] on linux
Type "help", "copyright", "credits" or "license" for more information.
>>>

To test whether you have the additional packages installed correctly, open
your favorite Python editor. If you don’t have one, you can elect to use Nano in
a Linux environment or even Notepad in a Windows environment. Type the
following:
#!/usr/bin/env python

import numpy as np
 Chapter 1 ■ Introduction to Cryptography and Python 7

import matplotlib.mlab as mlab

import matplotlib.pyplot as plt
mu, sigma = 100, 15
x = mu + sigma*np.random.randn(10000)
# the histogram of the data
n, bins, patches = plt.hist(x, 50, normed=1, facecolor='green',
alpha=0.75)
# add a 'best fit' line
y = mlab.normpdf( bins, mu, sigma)
l = plt.plot(bins, y, 'r--', linewidth=1)
plt.xlabel('Smarts')
plt.ylabel('Probability')
plt.title(r'$\mathrm{Histogram\ of\ IQ:}\ \mu=100,\ \sigma=15$')
plt.axis([40, 160, 0, 0.03])
plt.grid(True)
plt.show()

Save the file as matplot.py and execute the file. The preceding Python recipe
will generate a plot using NumPy and the Matplotlib library (see Figure 1.2).

Figure 1.2: Matplot.py test

Installing the Cryptography Package

Python has a Cryptography package that provides cryptographic recipes and
primitives to Python developers. It is designed to be your “cryptographic stan-
dard library.” As of this writing, it supports Python 2.7, Python 3.4+, and PyPy
5.4+. You can install the Cryptography package by using Pip3. The syntax is
as follows:
$ pip3 install cryptography
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