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Bulletproof SSL and TLS June Update: Cryptography, Protocol, and PKI

June 24, 2014

I've just released the June update of Bulletproof SSL and TLS. This batch completes the manuscript and brings about 80 new pages across three chapters:

  • Chapter 1, SSL, TLS, and Cryptography, begins with a brief introduction to SSL and TLS and discusses where these secure protocols fit in the Internet infrastructure. The remainder of this chapter provides a basic introduction to cryptography and discusses the classic cryptography threat model.
  • Chapter 2, Protocol, discusses the TLS protocol in detail. I cover TLS 1.2, with mentions of differences in earlier versions where appropriate. An overview of the protocol evolution over the years is included at the end for your reference.
  • Chapter 3, Public-Key Cryptography, is an introduction to Internet PKI, which is the predominant trust model on the Internet today. The focus is on the standards and organizations, as well as governance, weaknesses, and possible future improvements.

The manuscript is now complete and has slightly over 500 pages. Previous chapters include:

  • Chapter 4, Attacks against PKI, deals with attacks on trust. It covers all the major CA compromises as well as some other ways to subvert TLS authentication on the Internet.
  • Chapter 5, HTTP and Browser Issues, is all about the relationship between HTTP and SSL, the problems arising from the organic growth of the Web, and the messy interactions between different pieces of the web ecosystem.
  • Chapter 6, Implementation Flaws, deals with issues arising from design and programming mistakes related to random number generation, certificate validation, and other key TLS and PKI functionality. Additionally, it discusses voluntary protocol downgrade and truncation attacks.
  • Chapter 7, Protocol Attacks, is the longest chapter in the book at 60 pages. It covers all major protocol flaws discovered in recent years: Insecure Renegotiation, BEAST, CRIME, Lucky 13, RC4, TIME and BREACH, Triple Handshake, and the Bullrun program.
  • Chapter 8, Deployment, is the map for the entire book and provides step by step instructions on how to deploy secure and well-performing TLS servers and web applications.
  • Chapter 9, Performance, focuses on the speed of TLS, providing more detail as well as additional performance improvement techniques for those who want to squeeze every bit of speed out of their servers.
  • Chapter 10, HSTS, CSP, and Pinning, covers some advanced topics that strengthen web applications, as well as pinning, which is a way of reducing the large attack surface imposed by our current PKI model.
  • Chapter 10, OpenSSL Cookbook, describes the most frequently used OpenSSL functionality, largely focusing on installation, configuration, and key and certificate management. This is the most polished chapter, given that it had been released as a standalone short book in May 2013, and then updated in October.
  • Chapter 11, Testing with OpenSSL, continues with OpenSSL and explains how to use its command-line tools to test server configuration. Even though it is often much easier to use an automated tool for testing (e.g., the SSL Labs Server Test), OpenSSL remains the de facto standard for troubleshooting.
  • Chapter 12, Configuring Apache, discusses the SSL configuration of Apache httpd.
  • Chapter 13, Configuring Java and Tomcat, covers the current versions of Java and Tomcat, and provides full coverage of the SSL/TLS capabilities of Java 7 and 8.
  • Chapter 14, Configuring Microsoft Windows and IIS, discusses the Microsoft Windows platform and the Internet Information Server.
  • Chapter 15, Configuring Nginx, discusses the Nginx web server, covering the features in the stable and development version equally.

In the next couple of weeks we'll be working the finishing touches and preparing the book for printing. After two years of writing, it's very exciting to be this close to the finish.

If you already have access to the book, here's the direct link to access the new content:


If you don't have the access yet, Bulletproof SSL and TLS is available now for early access and preorder, at a 10% discount:

MY BOOK: If you like this blog post, you will love Bulletproof TLS and PKI. For system administrators, developers, and IT security professionals, this book provides a comprehensive coverage of the ever-changing field of SSL/TLS and Internet PKI and will teach you everything you need to know to protect your systems from eavesdropping and impersonation attacks. It's available now.