理解与部署SSL/TLS和PKI：Bulletproof SSL和TLS指南

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"Bulletproof SSL and TLS" 是一本由 Ivan Ristić 所著的书籍，专注于探讨如何理解和部署 SSL/TLS 以及公钥基础设施（PKI）来保护服务器和Web应用程序的安全。这本书由 Feisty Duck Limited 出版，首次出版于2014年8月，并在2015年3月进行了更新。 SSL（Secure Sockets Layer）和TLS（Transport Layer Security）是网络安全领域中至关重要的协议，它们主要负责在网络通信中提供数据加密、身份验证以及消息完整性的保障。这些协议广泛应用于网页浏览、电子邮件、在线交易等各种需要保护数据隐私的场景。本书的主要内容可能包括以下知识点： 1. **SSL/TLS 协议基础**：解释 SSL/TLS 的工作原理，包括握手过程、加密算法的选择、证书的使用以及会话管理等。 2. **公钥基础设施 (PKI)**：介绍 PKI 的构成，如证书颁发机构（CA）、证书撤销列表（CRL）和在线证书状态协议（OCSP），以及如何建立和管理自己的 PKI。 3. **安全配置**：讨论最佳实践，如何正确配置 SSL/TLS 服务器以防止常见的安全漏洞，如心脏出血（Heartbleed）等。 4. **证书管理**：阐述如何申请、安装、更新和撤销SSL/TLS证书，以及如何处理证书过期和信任问题。 5. **性能优化**：探讨如何通过调整参数和选择合适的加密套件来提高 SSL/TLS 连接的性能，减少延迟。 6. **移动设备与SSL/TLS**：针对移动平台的特性，讨论其对 SSL/TLS 支持的特殊考虑和优化。 7. **攻击与防御**：分析常见的 SSL/TLS 攻击方式，如中间人攻击、会话劫持等，以及如何通过安全策略和技术来防范这些攻击。 8. **合规性**：介绍与 SSL/TLS 相关的法规和标准，如 PCI DSS（支付卡行业数据安全标准）等，以及如何满足这些合规要求。 9. **监控与日志**：讲解如何监控 SSL/TLS 服务器的状态，记录和分析日志，以便及时发现并解决问题。 10. **未来趋势**：可能涵盖 SSL/TLS 的最新发展，如 TLS 1.3 版本的新特性，以及量子计算对现有加密技术的潜在威胁。这本书对于网络管理员、系统架构师、开发人员以及任何关心网络安全的读者来说，都是深入理解 SSL/TLS 技术及其应用的重要参考资料。通过阅读本书，读者将能够更好地保护他们的服务器和Web应用程序，确保用户数据的安全传输。

Preface

You are about to undertake a journey into the mysterious world of cryptography. I’ve just

completed mine—writing this book—and it’s been an amazing experience. Although I’d

been a user of SSL since its beginnings, I developed a deep interest in it around 2004, when I

started to work on my rst book, Apache Security. About ve years later, in 2009, I was look-

ing for something new to do; I decided to spend more time on SSL, and I’ve been focusing

on it ever since. e result is this book.

My main reason to go back to SSL was the thought that I could improve things. I saw an

important technology hampered by a lack of tools and documentation. Cryptography is a

fascinating subject: it’s a

eld in which when you know more, you actually know less. Or, in

other words, the more you know, the more you discover how much you don’t know. I can’t

count how many times I’ve had the experience of reaching a new level of understanding of a

complex topic only to have yet another layer of complexity open up to me; that’s what makes

the subject amazing.

I spent about two years writing this book. At rst, I thought I’d be able to spread the eort

so that I wouldn’t have to dedicate my life to it, but that wouldn’t work. At some point, I

realized that things are changing so quickly that I constantly need to go back and rewrite the

“nished” chapters. Towards the end, about six months ago, I started to spend every spare

moment writing to keep up.

I wrote this book to save you time. I spent the large part of the last ve years learning every-

thing I could about SSL/TLS and PKI, and I knew that only a few can aord to do the same.

I thought that if I put the most important parts of what I know into a book others might be

able to achieve a similar level of understanding in a fraction of the time—and here we are.

is book has the word “bulletproof” in the title, but that doesn’t mean that TLS is unbreak-

able. It does mean that if you follow the advice from this book you’ll be able to get the most

out of TLS and deploy it as securely as anyone else in the world. It’s not always going to be

easy—especially with web applications—but if you persist, you’ll have better security than

99.99% of servers out there. In fact, even with little eort, you can actually have better secu-

rity than 99% of the servers on the Internet.

Broadly speaking, there are two paths you can take to read this book. One is to take it easy

and start from the beginning. If you have time, this is going to be the more enjoyable ap-

proach. But if you want answers quickly, jump straight to chapters 8 and 9. ey’re going to

tell you everything you need to know about deploying secure servers while achieving good

performance. Aer that, use chapters 1 through 7 as a reference and chapters 10 through 16

for practical advice as needed.

Scope and Audience

is book exists to document everything you need to know about SSL/TLS and PKI for

practical, daily work. I aimed for just the right mix of theory, protocol detail, vulnerability

and weakness information, and deployment advice to help you get your job done.

As I was writing the book, I imagined representatives of three diverse groups looking over

my shoulder and asking me questions:

System administrators

Always pressed for time and forced to deal with an ever-increasing number of securi-

ty issues on their systems, system administrators need reliable advice about TLS so

that they can deal with its

conguration quickly and eciently. Turning to the Web

for information on this subject is counterproductive, because there’s so much incor-

rect and obsolete documentation out there.

Developers

Although SSL initially promised to provide security transparently for any TCP-based

protocol, in reality developers play a

signicant part in ensuring that applications re-

main secure. is is particularly true for web applications, which evolved around SSL

and TLS and incorporated features that can subvert them. In theory, you “just enable

encryption”; in practice, you enable encryption but also pay attention to a dozen or so

issues, ranging from small to big, that can break your security. In this book, I made a

special eort to document every single one of those issues.

Managers

Last but not least, I wrote the book for managers who, even though not necessarily

involved with the implementation, still have to understand what’s going on and make

decisions. e security space is getting increasingly complicated, so understanding

the attacks and threats is oen a job in itself. Oen, there isn’t any one way to deal

with the situation, and the best way oen depends on the context.

Overall, you will

nd very good coverage of HTTP and web applications here but little to no

mention of other protocols. is is largely because HTTP is unique in the way it uses en-

cryption, powered by browsers, which have become the most popular application-delivery

platform we’ve ever had. With that power come many problems, which is why there is so

much space dedicated to HTTP.

xvi

Preface

But don’t let that deceive you; if you take away the HTTP chapters, the remaining content

(about two-thirds of the book) provides generic advice that can be applied to any protocol

that uses TLS. e OpenSSL, Java, and Microso chapters provide protocol-generic infor-

mation for their respective platforms.

at said, if you’re looking for conguration examples for products other than web servers

you won’t nd them in this book. e main reason is that—unlike with web servers, for

which the market is largely split among a few major platforms—there are a great many

products of other types. It was quite a challenge to keep the web server advice up-to-date,

being faced with nearly constant changes. I wouldn’t be able to handle a larger scope. ere-

fore,

my intent is to publish additional conguration examples online and hopefully provide

the initial spark for a community to form to keep the advice up-to-date.

Contents

is book has 16 chapters, which can be grouped into several parts. e parts build on one

another to provide a complete picture, starting with theory and ending with practical ad-

vice.

e rst part, chapters 1 through 3, is the foundation of the book and discusses cryptogra-

phy, SSL, TLS, and PKI:

• Chapter 1, SSL, TLS, and Cryptography, begins with an introduction to SSL and TLS

and discusses where these secure protocols t in the Internet infrastructure. e re-

mainder of the chapter provides an introduction to cryptography and discusses the

classic threat model of the active network attacker.

• Chapter 2, Protocol, discusses the details of the TLS protocol. I cover TLS 1.2, which is

the most recent version. Information about earlier protocol revisions is provided where

appropriate. An overview of the protocol evolution from SSL 3 onwards is included at

the end for reference.

• Chapter 3, Public-Key Infrastructure, is an introduction to Internet PKI, which is the

predominant trust model used on the Internet today.

e focus is on the standards and

organizations as well as governance, ecosystem weaknesses and possible future im-

provements.

e second part, chapters 4 through 7, details the various problems with trust infrastruc-

ture, our security protocols, and their implementations in libraries and programs:

• Chapter 4, Attacks against PKI, deals with attacks on the trust ecosystem. It covers all

the major CA compromises, detailing the weaknesses, attacks, and consequences.

is

chapter gives a thorough historical perspective on the security of the PKI ecosystem,

which is important for understanding its evolution.

Contents

xvii

• Chapter 5, HTTP and Browser Issues, is all about the relationship between HTTP and

TLS, the problems arising from the organic growth of the Web, and the messy interac-

tions between dierent pieces of the web ecosystem.

• Chapter 6, Implementation Issues, deals with issues arising from design and program-

ming mistakes related to random number generation, certicate validation, and other

key TLS and PKI functionality. In addition, it discusses voluntary protocol downgrade

and truncation attacks and also covers Heartbleed.

• Chapter 7, Protocol Attacks, is the longest chapter in the book. It covers all the major

protocol

aws discovered in recent years: insecure renegotiation, BEAST, CRIME,

Lucky 13, RC4, TIME and BREACH, and Triple Handshake Attack. A brief discussion

of Bullrun and its impact on the security of TLS is also included.

e third part, chapters 8 through 10, provides comprehensive advice about deploying TLS

in a secure and ecient fashion:

• Chapter 8, Deployment, is the map for the entire book and provides step-by-step in-

structions on how to deploy secure and well-performing TLS servers and web applica-

tions.

• Chapter 9, Performance Optimization, focuses on the speed of TLS, going into great de-

tail about various 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, such as HTTP Strict Transport Security and Content Security Policy. It

also covers pinning, which is an eective way of reducing the large attack surface im-

posed by our current PKI model.

e fourth and nal part consists of chapters 11 through 16, which give practical advice

about how to use and congure TLS on major deployment platforms and web servers and

how to use OpenSSL to probe server conguration:

• Chapter 11, OpenSSL, describes the most frequently used OpenSSL functionality, with

a focus on installation, conguration, and key and certicate management. e last

section in this chapter provides instructions on how to construct and manage a private

certication authority.

• Chapter 12, Testing with OpenSSL, continues with OpenSSL and explains how to use its

command-line tools to test server conguration. Even though it’s oen much easier to

use an automated tool for testing, OpenSSL remains the tool you turn to when you

want to be sure about what’s going on.

•

Chapter 13, Conguring Apache, discusses the TLS conguration of the popular

Apache httpd web server. is is the rst in a series of chapters that provide practical

advice to match the theory from the earlier chapters. Each chapter is dedicated to one

major technology segment.

xviii

Preface

• Chapter 14, Conguring Java and Tomcat, covers Java (versions 7 and 8) and the Tom-

cat web server. In addition to conguration information, this chapter includes advice

about securing web applications.

• Chapter 15, Conguring Microso Windows and IIS, discusses the deployment of TLS

on the Microso Windows platform and the Internet Information Server. is chapter

also gives advice about the use of TLS in web applications running under ASP.NET.

• Chapter 16, Conguring Nginx, discusses the Nginx web server, covering the features of

the recent stable versions as well as some glimpses into the improvements in the devel-

opment branch.

SSL versus TLS

It is unfortunate that we have two names for essentially the same protocol. In my experi-

ence, most people are familiar with the name SSL and use it in the context of transport layer

encryption. Some people, usually those who spend more time with the protocols, use or try

to make themselves use the correct name, whichever is right in the given context. It’s proba-

bly a lost cause. Despite that, I tried to do the same. It was a bit cumbersome at times, but I

think I managed it by (1) avoiding either name where possible, (2) mentioning both where

advice applies to all versions, and

(3) using TLS in all other cases. You probably won’t no-

tice, and that’s ne.

SSL Labs

SSL Labs (www.ssllabs.com) is a research project I started in 2009 to focus on the practical

aspects of SSL/TLS and PKI. I joined Qualys in 2010, taking the project with me. Initially,

my main duties were elsewhere, but, as of 2014, SSL Labs has my full attention.

e project largely came out of my realization that the lack of good documentation and

tools is a large part of why TLS servers are generally badly congured. (Poor default settings

being the other major reason.) Without visibility—I thought—we can’t begin to work to

solve the problem. Over the years, SSL Labs expanded into four key projects:

Server test

e main feature of SSL Labs is the server test, which enables site visitors to check the

conguration of any public web server. e test includes dozens of important checks

not available elsewhere and gives a comprehensive view of server conguration. e

grading system is easy to understand and helps those who are not security experts

dierentiate between small and big issues. One of the most useful parts of the test is

the handshake simulator, which predicts negotiated protocols and cipher suites with

about 40 of the most widely used programs and devices. is feature eectively takes

the guesswork out of TLS conguration. In my opinion, it’s indispensable.

SSL versus TLS

xix

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