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 Implementing
Cryptography Using
Python®
Shannon W. Bray
Published by
John Wiley & Sons, Inc.
10475 Crosspoint Boulevard
Indianapolis, IN 46256
www.wiley.com

Copyright © 2020 by John Wiley & Sons, Inc., Indianapolis, Indiana

Published simultaneously in Canada

ISBN: 978-1-119-61220-9

ISBN: 978-1-119-61222-3 (ebk)

ISBN: 978-1-119-61545-3 (ebk)

Manufactured in the United States of America

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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
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