Bulletproof SSL and TLS: Understanding and Deploying SSL/TLS and PKI to Secure Servers and Web Applications

Background: Linux Admin.Disclaimer: I skipped the Microsoft IIS hardening chapter.I read the Amazon reviews of this book before buying it, and I was a bit skeptical. However my skepticism was wrong; this book should be reference material for any sysadmin or developer. It really is that good.I won't bother with the chapter-by-chapter synopsis. All you need to know is if you are interested in SSL/TLS, encryption, relevant hardening techniques and testing/verification (mainly via OpenSSL), etc., then this book is for you. The author runs SSLlabs. If you have ever tested your public site for BEAST,POODLE, etc., chances are you have used his site.Things this book does really well:- Give a comprehensive view of encryption, known weaknesses and attacks, and implementation suggestions and tips. I really can't think of a systems or programming book that nails a relatively niche subtopic in IT as well.- The author does a very good job of giving concrete real-world examples wherever and whenever possible.- While pretty technical, the language used in the book is pretty conversant. There is very little "hard math" if that's a concern.- The author is clearly an expert in SSL/TLS encryption. It is rare to read an introduction to normally rehashed material and say to yourself, 'Wait, it's THAT guy?"- Brings up Linux, OSX and Windows-specific notes. Conceptually the book is platform agnostic though. It is a nice mix between theoretical and practical.Thing that this book falls short on (keep in mind, these are very minor...not enough even to dock it a star):- The content is a bit stale. The original was published in 2014 and the first revision in 2015. Now that it is 2017, updated notes on the topics listed above would be nice, especially regarding suggested cipher suites, etc. However I know this is very hard in technical print media.- The amount of footnotes is staggering. The footnotes are practically all URL-shortened links to reference material. That's far from a bad thing normally, however they probably average out to 1-2 a page. It is not feasible to read them all.This is seriously a great book on SSL/TLS encryption. It should be required for any graduating CS/S college types, any professional sysadmin regardless of their OS, anyone in the IT/IS security world, and any developer that plans on releasing code that will ever touch a networkEncryption isn't going away. It is in everyone's interest listed above to get familiar with the details of TLS unless they want to end up with a compromised app or website.

This book is an awesome resource for understanding the theory and practical use of SSL/TLS! Topics include: the SSL/TLS protocol itself (concepts, messages over the wire, encryption methods), certificates (manual creation, acquiring from Certificate Authorities, extracting information), and configuring various web servers (Apache, Nginx, IIS), applications (OpenSSL command-line app), etc. Different web hosting scenarios, like shared hosting, virtual private server, and dedicated hosting, are discussed with respect to certificates and SSL/TLS connection establishment.Also, one extremely nice aspect of this book is the very deep and comprehensive descriptions of all the major exploited flaws in the history of the protocol -- including, importantly, exploits which are likely to plague implementations which are still in the wild. Given that the whole purpose of SSL/TLS is secure communication, it is crucial to understand all of its implementation flaws over its history (SSL 1/2/3, TLS 1.0,1.1,1.2,1.3(draft)). Reading the detailed accounts in the book of the exploits makes it clear how careful one must be with particular aspects of the protocol (e.g., initial handshake, encryption negotiation, ongoing sequence of packets). The fiascos resulting from poor initialization vector choices, negotiation to weak encryption algorithms, block-based encryption mistakes (chaining, padding issues), and hilariously cool information leaks (from compression, encryption output bit value biases, and timing attacks), provide dramatic and convincing proof that not using TLS 1.2 today (and soon TLS 1.3 (incomplete draft in January 2018)) would be foolish. Just look at the table of web-browser vulnerabilities in the Wikipedia article for SSL/TLS!The book's description of some vulnerabilities does not shy away from mentioning some scandalous dynamics (e.g., government payments, corrupt certificate authorities, etc.) which affected, and likely continue to affect, the evolution of SSL/TLS. The details in the book can help gain a clear understanding of the past and potential weaknesses of TLS. The final page of the book rhetorically asks if TLS is actually secure, or if it is "irreparably broken and doomed", and argues persuasively that TLS is a success, but notes that careful attention is required in our "harsh reality of widespread mass surveillance".This excellent book covers seemingly everything about SSL/TLS for theory and actual practice (applications, configurations, command-line tools, certificate ecosystem).[Aside: If you are a software developer with proficiency in "C", and an interest in actual implementation of aspects of SSL/TLS with corresponding theory and discussion, then I recommend the excellent book "Implementing SSL/TLS" by Joshua Davies (which I also purchased from Amazon). That book, and the "Bulletproof SSL and TLS" book reviewed here, are perfect complements to each other.]

I am a network engineer who recently started learning security implementations side of the network. I had no previous knowledge regarding security, and this book is a great way to start learning it. I used this book in conjunction with the Understand Cryptography by Christof Paar. I read the first several chapters in this book. (It gives you a great overview of most of the security primitives), then I read through the Understand Cryptography book, then I jumped back to this book and read the rest of the chapters. I feel much more confident regarding my understanding of internet security/cryptography implementation now after reading these two books.

This is one of the best and most comprehensive tomes on SSL/TLS out there. It explains things to people like me, who don't have a PhD in mathematics or encryption. I'm trying to better understand the why's and how's of the security devices that I configure and build and this book gave me a better foundation than any website or instruction manual I've found thus far.

If you're involved with technology on any level, encryption is here to stay and it's only going to get more complicated. Somehow Ivan wrote a real page turner that can be used as both a point of reference and read from cover to cover with ease. Every page reveals more about what I don't know and anyone experienced in the industry will appreciate the feeling as you can't fix what you don't know is broke (yourself - before reading this book).