Book Image

Demystifying Cryptography with OpenSSL 3.0

By : Alexei Khlebnikov
Book Image

Demystifying Cryptography with OpenSSL 3.0

By: Alexei Khlebnikov

Overview of this book

Security and networking are essential features of software today. The modern internet is full of worms, Trojan horses, men-in-the-middle, and other threats. This is why maintaining security is more important than ever. OpenSSL is one of the most widely used and essential open source projects on the internet for this purpose. If you are a software developer, system administrator, network security engineer, or DevOps specialist, you’ve probably stumbled upon this toolset in the past – but how do you make the most out of it? With the help of this book, you will learn the most important features of OpenSSL, and gain insight into its full potential. This book contains step-by-step explanations of essential cryptography and network security concepts, as well as practical examples illustrating the usage of those concepts. You’ll start by learning the basics, such as how to perform symmetric encryption and calculate message digests. Next, you will discover more about cryptography: MAC and HMAC, public and private keys, and digital signatures. As you progress, you will explore best practices for using X.509 certificates, public key infrastructure, and TLS connections. By the end of this book, you’ll be able to use the most popular features of OpenSSL, allowing you to implement cryptography and TLS in your applications and network infrastructure.
Table of Contents (20 chapters)
1
Part 1: Introduction
3
Part 2: Symmetric Cryptography
8
Part 3: Asymmetric Cryptography and Certificates
12
Part 4: TLS Connections and Secure Communication
16
Part 5: Running a Mini-CA

Establishing a TLS client connection on the command line

To establish a TLS client connection, we will use the s_client subcommand of the openssl tool. Its documentation can be found on its man page:

$ man openssl-s_client

There is an HTTPS server on the internet to use as an example, https://example.org/. Let’s connect to it via TLS and get its home page:

$ openssl s_client -connect example.org:443

The openssl tool will output a lot of information about how the TLS handshaking has gone, which cryptographic algorithms were used, and even the base64-encoded server certificate will be printed.

We can also request verification of the server certificate and its hostname by adding the -verify_return_error and -verify_hostname command-line options:

$ openssl s_client \
    -connect example.org:443 \
    -verify_return_error \
    -verify_hostname example.org

If you want to verify the server certificate...