Network Security with OpenSSL (John Viega, Matt Messier, Pravir Chandra) (Z-Library)

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Table of Contents Network Security with OpenSSL By Pravir Chandra, Matt Messier, John Viega Publisher : O'Reilly Pub Date : June 2002 ISBN : 0-596-00270-X Pages : 384 OpenSSL is a popular and effective open source version of SSL/TLS, the most widely used protocol for secure network communications. The only guide available on the subject, Network Security with OpenSSLdetails the challenges in securing network communications, and shows you how to use OpenSSL tools to best meet those challenges. Focused on the practical, this book provides only the information that is necessary to use OpenSSL safely and effectively. TE AM FL Y Team-Fly®

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ii Table of Content Table of Content ......................................................................................................ii Dedication .............................................................................................................vi Preface....................................................................................................................vii About This Book .............................................................................................. viii Conventions Used in This Book........................................................................x Comments and Questions ................................................................................xi Acknowledgments ..............................................................................................xi Chapter 1. Introduction ...........................................................................................1 1.1 Cryptography for the Rest of Us.................................................................1 1.2 Overview of SSL ...........................................................................................8 1.3 Problems with SSL .....................................................................................10 1.4 What SSL Doesn't Do Well .......................................................................16 1.5 OpenSSL Basics.........................................................................................17 1.6 Securing Third-Party Software .................................................................18 Chapter 2. Command-Line Interface..................................................................23 2.1 The Basics ...................................................................................................23 2.2 Message Digest Algorithms ......................................................................25 2.3 Symmetric Ciphers .....................................................................................27 2.4 Public Key Cryptography...........................................................................28 2.5 S/MIME.........................................................................................................32 2.6 Passwords and Passphrases ...................................................................33 2.7 Seeding the Pseudorandom Number Generator...................................35 Chapter 3. Public Key Infrastructure (PKI) ........................................................37 3.1 Certificates...................................................................................................37 3.2 Obtaining a Certificate ...............................................................................44 3.3 Setting Up a Certification Authority..........................................................47 Chapter 4. Support Infrastructure .......................................................................60 4.1 Multithread Support ....................................................................................60 4.2 Internal Error Handling...............................................................................66 4.3 Abstract Input/Output .................................................................................70 4.4 Random Number Generation ...................................................................80 4.5 Arbitrary Precision Math ............................................................................85 4.6 Using Engines .............................................................................................91 Chapter 5. SSL/TLS Programming.....................................................................93 5.1 Programming with SSL ..............................................................................93 5.2 Advanced Programming with SSL .........................................................125 Chapter 6. Symmetric Cryptography................................................................143 6.1 Concepts in Symmetric Cryptography...................................................143 6.2 Encrypting with the EVP API ..................................................................145 6.3 General Recommendations ....................................................................161 Chapter 7. Hashes and MACs ..........................................................................162 7.1 Overview of Hashes and MACs .............................................................162 7.2 Hashing with the EVP API.......................................................................163 7.3 Using MACs...............................................................................................168 7.4 Secure HTTP Cookies .............................................................................179 Chapter 8. Public Key Algorithms.....................................................................184

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iii 8.1 When to Use Public Key Cryptography.................................................184 8.2 Diffie-Hellman............................................................................................185 8.2 Diffie-Hellman............................................................................................190 8.3 Digital Signature Algorithm (DSA)..........................................................195 8.4 RSA.............................................................................................................200 8.5 The EVP Public Key Interface ................................................................205 8.6 Encoding and Decoding Objects............................................................213 Chapter 9. OpenSSL in Other Languages ......................................................220 9.1 Net::SSLeay for Perl ................................................................................220 9.2 M2Crypto for Python ................................................................................225 9.3 OpenSSL Support in PHP.......................................................................233 Chapter 10. Advanced Programming Topics..................................................241 10.1 Object Stacks ..........................................................................................241 10.2 Configuration Files .................................................................................242 10.3 X.509 ........................................................................................................245 10.4 PKCS#7 and S/MIME ............................................................................259 10.5 PKCS#12 .................................................................................................268 Appendix A. Command-Line Reference ..........................................................270 asn1parse............................................................................................................270 ca ........................................................................................................................271 ciphers ................................................................................................................277 crl .......................................................................................................................277 crl2pkcs7 ............................................................................................................279 dgst .....................................................................................................................280 dhparam..............................................................................................................281 dsa ......................................................................................................................282 dsaparam ............................................................................................................284 enc ......................................................................................................................285 errstr ...................................................................................................................287 gendsa ................................................................................................................287 genrsa .................................................................................................................288 nseq ....................................................................................................................289 passwd................................................................................................................289 pkcs7 ..................................................................................................................290 pkcs8 ..................................................................................................................291 pkcs12 ................................................................................................................293 rand ....................................................................................................................296 req ......................................................................................................................296 rsa.......................................................................................................................301 rsautl...................................................................................................................302 s_client ...............................................................................................................304 s_server ..............................................................................................................306 s_time.................................................................................................................309 sess_id ................................................................................................................311 smime.................................................................................................................312 speed ..................................................................................................................316 spkac ..................................................................................................................316 verify ..................................................................................................................317 version................................................................................................................318 x509....................................................................................................................319

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iv Colophon ..............................................................................................................326

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v Copyright © 2002 O'Reilly & Associates, Inc. All rights reserved. Printed in the United States of America. Published by O'Reilly & Associates, Inc., 1005 Gravenstein Highway North, Sebastopol, CA 95472. O'Reilly & Associates books may be purchased for educational, business, or sales promotional use. Online editions are also available for most titles (http://safari.oreilly.com). For more information contact our corporate/institutional sales department: 800-998-9938 or corporate@oreilly.com. The O'Reilly logo is a registered trademark of O'Reilly & Associates, Inc. Many of the designations used by manufacturers and sellers to distinguish their products are claimed as trademarks. Where those designations appear in this book, and O'Reilly & Associates, Inc. was aware of a trademark claim, the designations have been printed in caps or initial caps. The association between the image of a group of sea lions and seals and the topic of network security with OpenSSL is a trademark of O'Reilly & Associates, Inc. While every precaution has been taken in the preparation of this book, the publisher and the author(s) assume no responsibility for errors or omissions, or for damages resulting from the use of the information contained herein.

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vi Dedication To the memory of Arthur J. Zoebelein, former Chief of the Office of Cryptologic Archives and History, National Security Agency

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vii Preface About This Book Conventions Used in This Book Comments and Questions Acknowledgments

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viii About This Book The Internet is a dangerous place, more dangerous than most people realize. Many technical people know that it's possible to intercept and modify data on the wire, but few realize how easy it actually is. If an application doesn't properly protect data when it travels an untrusted network, the application is a security disaster waiting to happen. The SSL (Secure Socket Layer) protocol and its successor TLS (Transport Layer Security) can be used to secure applications that need to communicate over a network. OpenSSL is an open source library that implements the SSL and TLS protocols, and is by far the most widely deployed, freely available implementation of these protocols. OpenSSL is fully featured and cross-platform, working on Unix and Windows alike. It's primarily used from C and C++ programs, but you can use it from the command line (see Chapter 1 through Chapter 3) and from other languages such as Python, Perl, and PHP (see Chapter 9). In this book, we'll teach developers and administrators how to secure applications with OpenSSL. We won't just show you how to SSL-enable your applications, we'll be sure to introduce you to the most significant risks involved in doing so, and the methods for mitigating those risks. These methods are important; it takes more work to secure an SSL-enabled application than most people think, especially when code needs to run in multithreaded, highly interoperable environments where efficiency is a concern. OpenSSL is more than just a free implementation of SSL. It also includes a general-purpose cryptographic library, which can be useful for situations in which SSL isn't an appropriate solution. Working with cryptography at such a low level can be dangerous, since there are many pitfalls in applying cryptography of which few developers are fully aware. Nonetheless, we do discuss the available functionality for those that wish to use it. Additionally, OpenSSL provides some high- level primitives, such as support for the S/MIME email standard. The bulk of this book describes the OpenSSL library and the many ways to use it. We orient the discussion around working examples, instead of simply providing reference material. We discuss all of the common options OpenSSL users can support, as well as the security implications of each choice. Depending on your needs, you may end up skipping around in this book. For people who want to use OpenSSL from the command line for administrative tasks, everything they need is in the first three chapters. Developers interested in SSL-enabling an application can probably read Chapter 1, then skip directly to Chapter 5 (though they will have to refer to parts of Chapter 4 to understand all the code). Here's an overview of the book's contents: Chapter 1 This chapter introduces SSL and the OpenSSL library. We give an overview of the biggest security risks involved with deploying the library and discuss how to mitigate them at a high level. We also look at how to use OpenSSL along with Stunnel to secure third-party software, such as POP servers that don't otherwise have built-in SSL support. Chapter 2 Here we discuss how to use basic OpenSSL functionality from the command line, for those who wish to use OpenSSL interactively, call out to it from shell scripts, or interface with it from languages without native OpenSSL support.

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ix Chapter 3 This chapter explains the basics of Public Key Infrastructure (PKI), especially as it manifests itself in OpenSSL. This chapter is primarily concerned with how to go about getting certificates for use in SSL, S/MIME, and other PKI-dependent cryptography. We also discuss how to manage your own PKI using the OpenSSL command line, if you so choose. Chapter 4 In this chapter, we talk about the various low-level APIs that are most important to OpenSSL. Some of these APIs need to be mastered in order to make full use of the OpenSSL library. Particularly, we lay the foundation for enabling multithreaded application support and performing robust error handling with OpenSSL. Additionally, we discuss the OpenSSL IO API, its randomness API, its arbitrary precision math API, and how to use cryptographic acceleration with the library. Chapter 5 Here we discuss the ins and outs of SSL-enabling applications, particularly with SSLv3 and its successor, TLSv1. We not only cover the basics but also go into some of the more obscure features of these protocols, such as session resumption, which is a tool that can help speed up SSL connection times in some circumstances. Chapter 6 This chapter covers everything you need to know to use OpenSSL's interface to secret- key cryptographic algorithms such as Triple DES, RC4, and AES (the new Advanced Encryption Standard). In addition to covering the standard API, we provide guidelines on selecting algorithms that you should support for your applications, and we explain the basics of these algorithms, including different modes of operation, such as counter mode. Additionally, we talk about how to provide some security for UDP-based traffic, and discuss general considerations for securely integrating symmetric cryptography into your applications. Chapter 7 In this chapter, we discuss how to use nonreversible (one-way) cryptographic hash functions, often called message digest algorithms. We also show how to use Message Authentication Codes (MACs), which can be used to provide data integrity via a shared secret. We show how to apply MACs to ensure that tampering with HTTP cookies will be detected. Chapter 8 Here we talk about the various public key algorithms OpenSSL exports, including Diffie- Hellman key exchange, the Digital Signature Algorithm (DSA), and RSA. Additionally, we discuss how to read and write common storage formats for public keys. Chapter 9 This chapter describes how to use OpenSSL programmatically from Perl using the Net::SSLeay package, from Python using the M2Crypto library, and from PHP. Chapter 10

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x In this chapter, we discuss many of the more esoteric parts of the OpenSSL API that are still useful, including the OpenSSL configuration API, creating and using S/MIME email, and performing certificate management programmatically. Appendix A Here we provide a reference to the many options in the OpenSSL command-line interface. Additionally, the book's web site (http://www.opensslbook.com) contains API reference material that supplements this book. We also give pointers to the official OpenSSL documentation. Note that we do not cover using SSL from Apache. While Apache does use OpenSSL for its cryptography, it provides its own API for configuring everything. Covering that isn't in the scope of this book. Refer to the Apache documentation, or the book Apache: The Definitive Guide by Ben Laurie and Peter Laurie (O'Reilly & Associates). As we finish this book, OpenSSL is at Version 0.9.6c, and 0.9.7 is in feature freeze, though a final release is not expected until well after this book's publication. Additionally, we expect developers to have to interoperate with 0.9.6 for some time. Therefore, we have gone out of our way to support both versions. Usually, our discussion will apply to both 0.9.6 and 0.9.7 releases unless otherwise noted. If there are features that were experimental in 0.9.6 and changed significantly in 0.9.7 (most notably support for hardware acceleration), we tend to explain only the 0.9.7 solution. We've set up a web site at www.opensslbook.com. It contains an up-to-date archive of all the example code used in this book. All the examples have been tested with the appropriate version of OpenSSL on Mac OS X, FreeBSD, Linux, and Windows 2000. They're expected to work portably in any environment that supports OpenSSL. In addition, the web site contains API reference documentation. Because OpenSSL contains literally thousands of functions, we thought it best to offload such documentation to the Web, especially considering that many of the APIs are still evolving. The book's web site also contains links to related secure programming resources and will contain an errata listing of any problems that are found after publication. You can contact the authors by email at authors@opensslbook.com. Conventions Used in This Book The following conventions are used in this book: Italic Used for filenames, directory names, and URLs. It is also used to emphasize new terms and concepts when they are introduced. Constant Width Used for commands, attributes, variables, code examples, and system output. Constant Width Italic

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xi Used in syntax descriptions to indicate user-defined items. Constant Width Bold Indicates user input in examples showing an interaction. Also indicates emphasized code elements to which you should pay particular attention. Indicates a tip, suggestion, or general note. Indicates a warning or caution. Comments and Questions We have tested and verified the information in this book to the best of our ability, but you may find that features have changed or that we have made mistakes. If so, please notify us by writing to: O'Reilly & Associates, Inc. 1005 Gravenstein Highway North Sebastopol, CA 95472 (800) 998-9938 (in the United States or Canada) (707) 829-0515 (international or local) (707) 829-0104 (fax) To ask technical questions or comment on the book, send email to: bookquestions@oreilly.com We have a web site for this book, where you can find examples and errata (previously reported errors and corrections are available for public view there). You can access this page at: http://www.oreilly.com/catalog/openssl/ For more information about this book and others, see the O'Reilly web site: http://www.oreilly.com Acknowledgments We'd like to thank everyone who has contributed to this book, either directly or indirectly. Everyone at O'Reilly has been very helpful, particularly Julie Flanagan, and Kyle Hart, and our editor Robert Denn. All of our co-workers at Secure Software Solutions have been extremely tolerant of our work on this book and have helped us out whenever necessary. Particularly, we'd like to thank Zachary TE AM FL Y Team-Fly®

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xii Girouard, Jamie McGann, Michael Shinn, Scott Shinn, Grisha Trubetskoy, and Robert Zigweid for their direct support. As with our co-workers, we'd like to thank all of our family and friends for their tolerance, support and enthusiasm, particularly our parents, Anne, Emily, and Molly Viega, Ankur Chandra, Nupur Chandra, Sara Elliot, Bob Fleck, Shawn Geddis, Tom O'Connor, Bruce Potter, Greg Pryzby, George Reese, Ray Schneider, and John Steven. We'd particularly like to thank the people who reviewed this book, including Simson Garfinkel, Russ Housley, Lutz Jänicke, and Stefan Norberg. Their input was highly valuable across the board. Everyone who has contributed to what is now OpenSSL deserves special thanks, including Mark Cox, Ralf Engelschall, Dr. Stephen Henson, Tim Hudson, Lutz Jänicke, Ben Laurie, Richard Levitte, Bodo Möller, Ulf Möller, Andy Polyakov, Holger Reif, Paul Sutton, Geoff Thorpe, and Eric A. Young. We also thank Sue Miller for encouraging us to write this book in the first place. —John Viega, Matt Messier, and Pravir Chandra March 2002 Fairfax, VA

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1 Chapter 1. Introduction In today's networked world, many applications need security, and cryptography is one of the primary tools for providing that security. The primary goals of cryptography, data confidentiality, data integrity, authentication, and non-repudiation (accountability) can be used to thwart numerous types of network-based attacks, including eavesdropping, IP spoofing, connection hijacking, and tampering. OpenSSL is a cryptographic library; it provides implementations of the industry's best-regarded algorithms, including encryption algorithms such as 3DES ("Triple DES"), AES and RSA, as well as message digest algorithms and message authentication codes. Using cryptographic algorithms in a secure and reliable manner is much more difficult than most people believe. Algorithms are just building blocks in cryptographic protocols, and cryptographic protocols are notoriously difficult to get right. Cryptographers have a difficult time devising protocols that resist all known attacks, and the average developer tends to do a lot worse. For example, developers often try to secure network connections simply by encrypting data before sending it, then decrypting it on receipt. That strategy often fails to ensure the integrity of data. In many situations, attackers can tamper with data, and sometimes even recover it. Even when protocols are well designed, implementation errors are common. Most cryptographic protocols have limited applicability, such as secure online voting. However, protocols for securely communicating over an insecure medium have ubiquitous applicability. That's the basic purpose of the SSL protocol and its successor, TLS (when we generically refer to SSL, we are referring to both SSL and TLS): to provide the most common security services to arbitrary (TCP-based) network connections in such a way that the need for cryptographic expertise is minimized. Ultimately, it would be nice if developers and administrators didn't need to know anything about cryptography or even security to protect their applications. It would be nice if security was as simple as linking in a different socket library when building a program. The OpenSSL library strives toward that ideal as much as possible, but in reality, even the SSL protocol requires a good understanding of security principles to apply securely. Indeed, most applications using SSL are susceptible to attack. Nonetheless, SSL certainly makes securing network connections much simpler. Using SSL doesn't require any understanding of how cryptographic algorithms work. Instead, you only need to understand the basic properties important algorithms have. Similarly, developers do not need to worry about cryptographic protocols; SSL doesn't require any understanding of its internal workings in order to be used. You only need to understand how to apply the algorithm properly. The goal of this book is to document the OpenSSL library and how to use it properly. This is a book for practitioners, not for security experts. We'll explain what you need to know about cryptography in order to use it effectively, but we don't attempt to write a comprehensive introduction on the subject for those who are interested in why cryptography works. For that, we recommend Applied Cryptography, by Bruce Schneier (John Wiley & Sons). For those interested in a more technical introduction to cryptography, we recommend Menezes, van Oorschot, and Vanstone's Handbook of Applied Cryptography (CRC Press). Similarly, we do not attempt to document the SSL protocol itself, just its application. If you're interested in the protocol details, we recommend Eric Rescorla's SSL and TLS (Addison-Wesley). 1.1 Cryptography for the Rest of Us For those who have never had to work with cryptography before, this section introduces you to the fundamental principles you'll need to know to understand the rest of the material in this book. First,

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2 we'll look at the problems that cryptography aims to solve, and then we'll look at the primitives that modern cryptography provides. Anyone who has previously been exposed to the basics of cryptography should feel free to skip ahead to the next section. 1.1.1 Goals of Cryptography The primary goal of cryptography is to secure important data as it passes through a medium that may not be secure itself. Usually, that medium is a computer network. There are many different cryptographic algorithms, each of which can provide one or more of the following services to applications: Confidentiality (secrecy) Data is kept secret from those without the proper credentials, even if that data travels through an insecure medium. In practice, this means potential attackers might be able to see garbled data that is essentially "locked," but they should not be able to unlock that data without the proper information. In classic cryptography, the encryption (scrambling) algorithm was the secret. In modern cryptography, that isn't feasible. The algorithms are public, and cryptographic keys are used in the encryption and decryption processes. The only thing that needs to be secret is the key. In addition, as we will demonstrate a bit later, there are common cases in which not all keys need to be kept secret. Integrity (anti-tampering) The basic idea behind data integrity is that there should be a way for the recipient of a piece of data to determine whether any modifications are made over a period of time. For example, integrity checks can be used to make sure that data sent over a wire isn't modified in transit. Plenty of well-known checksums exist that can detect and even correct simple errors. However, such checksums are poor at detecting skilled intentional modifications of the data. Several cryptographic checksums do not have these drawbacks if used properly. Note that encryption does not ensure data integrity. Entire classes of encryption algorithms are subject to "bit-flipping" attacks. That is, an attacker can change the actual value of a bit of data by changing the corresponding encrypted bit of data. Authentication Cryptography can help establish identity for authentication purposes. Non-repudiation Cryptography can enable Bob to prove that a message he received from Alice actually came from Alice. Alice can essentially be held accountable when she sends Bob such a message, as she cannot deny (repudiate) that she sent it. In the real world, you have to assume that an attacker does not compromise particular cryptographic keys. The SSL protocol does not support non-repudiation, but it is easily added by using digital signatures. These simple services can be used to stop a wide variety of network attacks, including: Snooping (passive eavesdropping) An attacker watches network traffic as it passes and records interesting data, such as credit card information.

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3 Tampering An attacker monitors network traffic and maliciously changes data in transit (for example, an attacker may modify the contents of an email message). Spoofing An attacker forges network data, appearing to come from a different network address than he actually comes from. This sort of attack can be used to thwart systems that authenticate based on host information (e.g., an IP address). Hijacking Once a legitimate user authenticates, a spoofing attack can be used to "hijack" the connection. Capture-replay In some circumstances, an attacker can record and replay network transactions to ill effect. For example, say that you sell a single share of stock while the price is high. If the network protocol is not properly designed and secured, an attacker could record that transaction, then replay it later when the stock price has dropped, and do so repeatedly until all your stock is gone. Many people assume that some (or all) of the above attacks aren't actually feasible in practice. However, that's far from the truth. Especially due to tool sets such as dsniff (http://www.monkey.org/~dugsong/dsniff/), it doesn't even take much experience to launch all of the above attacks if access to any node on a network between the two endpoints is available. Attacks are equally easy if you're on the same local network as one of the endpoints. Talented high school students who can use other people's software to break into machines and manipulate them can easily manage to use these tools to attack real systems. Traditionally, network protocols such as HTTP, SMTP, FTP, NNTP, and Telnet don't provide adequate defenses to the above attacks. Before electronic commerce started taking off in mid-1990, security wasn't really a large concern, especially considering the Internet's origins as a platform for sharing academic research and resources. While many protocols provided some sort of authentication in the way of password-based logins, most of them did not address confidentiality or integrity at all. As a result, all of the above attacks were possible. Moreover, authentication information could usually be among the information "snooped" off a network. SSL is a great boon to the traditional network protocols, because it makes it easy to add transparent confidentiality and integrity services to an otherwise insecure TCP-based protocol. It can also provide authentication services, the most important being that clients can determine if they are talking to the intended server, not some attacker that is spoofing the server. 1.1.2 Cryptographic Algorithms The SSL protocol covers many cryptographic needs. Sometimes, though, it isn't good enough. For example, you may wish to encrypt HTTP cookies that will be placed on an end user's browser. SSL won't help protect the cookies while they're being stored on that disk. For situations like this, OpenSSL exports the underlying cryptographic algorithms used in its implementation of the SSL protocol. Generally, you should avoid using cryptographic algorithms directly if possible. You're not likely to get a totally secure system simply by picking an algorithm and applying it. Usually,

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4 cryptographic algorithms are incorporated into cryptographic protocols. Plenty of nonobvious things can be wrong with a protocol based on cryptographic algorithms. That is why it's better to try to find a well-known cryptographic protocol to do what you want to do, instead of inventing something yourself. In fact, even the protocols invented by cryptographers often have subtle holes. If not for public review, most protocols in use would be insecure. Consider the original WEP protocol for IEEE 802.11 wireless networking. WEP (Wired Equivalent Privacy) is the protocol that is supposed to provide the same level of security for data that physical lines provide. It is a challenge, because data is transmitted through the air, instead of across a wire. WEP was designed by veteran programmers, yet without soliciting the opinions of any professional cryptographers or security protocol developers. Although to a seasoned developer with moderate security knowledge the protocol looked fine, in reality, it was totally lacking in security. Nonetheless, sometimes you might find a protocol that does what you need, but can't find an implementation that suits your needs. Alternatively, you might find that you do need to come up with your own protocol. For those cases, we do document the SSL cryptographic API. Five types of cryptographic algorithms are discussed in this book: symmetric key encryption, public key encryption, cryptographic hash functions, message authentication codes, and digital signatures. 1.1.2.1 Symmetric key encryption Symmetric key algorithms encrypt and decrypt data using a single key. As shown in Figure 1-1, the key and the plaintext message are passed to the encryption algorithm, producing ciphertext. The result can be sent across an insecure medium, allowing only a recipient who has the original key to decrypt the message, which is done by passing the ciphertext and the key to a decryption algorithm. Obviously, the key must remain secret for this scheme to be effective. Figure 1-1. Symmetric key cryptography The primary disadvantage of symmetric key algorithms is that the key must remain secret at all times. In particular, exchanging secret keys can be difficult, since you'll usually want to exchange keys on the same medium that you're trying to use encryption to protect. Sending the key in the

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5 clear before you use it leaves open the possibility of an attacker recording the key before you even begin to send data. One solution to the key distribution problem is to use a cryptographic key exchange protocol. OpenSSL provides the Diffie-Hellman protocol for this purpose, which allows for key agreement without actually divulging the key on the network. However, Diffie-Hellman does not guarantee the identity of the party with whom you are exchanging keys. Some sort of authentication mechanism is necessary to ensure that you don't accidentally exchange keys with an attacker. Right now, Triple DES (usually written 3DES, or sometimes DES3) is the most conservative symmetric cipher available. It is in wide use, but AES, the new Advanced Encryption Standard, will eventually replace it as the most widely used cipher. AES is certainly faster than 3DES, but 3DES has been around a lot longer, and thus is a more conservative choice for the ultra-paranoid. It is worth mentioning that RC4 is widely supported by existing clients and servers. It is faster than 3DES, but is difficult to set up properly (don't worry, SSL uses RC4 properly). For purposes of compatibility with existing software in which neither AES nor 3DES are supported, RC4 is of particular interest. We don't recommend supporting other algorithms without a good reason. For the interested, we discuss cipher selection in Chapter 6. Security is related to the length of the key. Longer key lengths are, of course, better. To ensure security, you should only use key lengths of 80 bits or higher. While 64-bit keys may be secure, they likely will not be for long, whereas 80-bit keys should be secure for at least a few years to come. AES supports only 128-bit keys and higher, while 3DES has a fixed 112 bits of effective security.[1] Both of these should be secure for all cryptographic needs for the foreseeable future. Larger keys are probably unnecessary. Key lengths of 56 bits (regular DES) or less (40-bit keys are common) are too weak; they have proven to be breakable with a modest amount of time and effort. [1] 3DES provides 168 bits of security against brute-force attacks, but there is an attack that reduces the effective security to 112 bits. The enormous space requirements for that attack makes it about as practical as brute force (which is completely impractical in and of itself). 1.1.2.2 Public key encryption Public key cryptography suggests a solution to the key distribution problem that plagues symmetric cryptography. In the most popular form of public key cryptography, each party has two keys, one that must remain secret (the private key) and one that can be freely distributed (the public key). The two keys have a special mathematical relationship. For Alice to send a message to Bob using public key encryption (see Figure 1-2), Alice must first have Bob's public key. She then encrypts her message using Bob's public key, and delivers it. Once encrypted, only someone who has Bob's private key can successfully decrypt the message (hopefully, that's only Bob). Figure 1-2. Public key cryptography

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6 Public key encryption solves the problem of key distribution, assuming there is some way to find Bob's public key and ensure that the key really does belong to Bob. In practice, public keys are passed around with a bunch of supporting information called a certificate, and those certificates are validated by trusted third parties. Often, a trusted third party is an organization that does research (such as credit checks) on people who wish to have their certificates validated. SSL uses trusted third parties to help address the key distribution problem. Public key cryptography has a significant drawback, though: it is intolerably slow for large messages. Symmetric key cryptography can usually be done quickly enough to encrypt and decrypt all the network traffic a machine can manage. Public key cryptography is generally limited by the speed of the cryptography, not the bandwidth going into the computer, particularly on server machines that need to handle multiple connections simultaneously. As a result, most systems that use public key cryptography, SSL included, use it as little as possible. Generally, public key encryption is used to agree on an encryption key for a symmetric algorithm, and then all further encryption is done using the symmetric algorithm. Therefore, public key encryption algorithms are primarily used in key exchange protocols and when non- repudiation is required. RSA is the most popular public key encryption algorithm. The Diffie-Hellman key exchange protocol is based on public key technology and can be used to achieve the same ends by exchanging a symmetric key, which is used to perform actual data encryption and decryption. For public key schemes to be effective, there usually needs to be an authentication mechanism involving a trusted third party that is separate from the encryption itself. Most often, digital signature schemes, which we discuss below, provide the necessary authentication. Keys in public key algorithms are essentially large numbers with particular properties. Therefore, bit length of keys in public key ciphers aren't directly comparable to symmetric algorithms. With public key encryption algorithms, you should use keys of 1,024 bits or more to ensure reasonable security. 512-bit keys are probably too weak. Anything larger than 2,048 bits may be too slow, and chances are it will not buy security that is much more practical. Recently, there's been some concern that 1,024-bit keys are too weak, but as of this writing, there hasn't been conclusive proof. Certainly, 1,024 bits is a bare minimum for practical security from short-term attacks. If your keys

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7 potentially need to stay protected for years, then you might want to go ahead and use 2,048-bit keys. When selecting key lengths for public key algorithms, you'll usually need to select symmetric key lengths as well. Recommendations vary, but we recommend using 1,024-bit keys when you are willing to work with symmetric keys that are less than 100 bits in length. If you're using 3DES or 128-bit keys, we recommend 2,048-bit public keys. If you are paranoid enough to be using 192-bit keys or higher, we recommend using 4,096-bit public keys. Requirements for key lengths change if you're using elliptic curve cryptography (ECC), which is a modification of public key cryptography that can provide the same amount of security using faster operations and smaller keys. OpenSSL currently doesn't support ECC, and there may be some lingering patent issues for those who wish to use it. For developers interested in this topic, we recommend the book Implementing Elliptic Curve Cryptography, by Michael Rosing (Manning). 1.1.2.3 Cryptographic hash functions and Message Authentication Codes Cryptographic hash functions are essentially checksum algorithms with special properties. You pass data to the hash function, and it outputs a fixed-size checksum, often called a message digest, or simply digest for short. Passing identical data into the hash function twice will always yield identical results. However, the result gives away no information about the data input to the function. Additionally, it should be practically impossible to find two inputs that produce the same message digest. Generally, when we discuss such functions, we are talking about one-way functions. That is, it should not be possible to take the output and algorithmically reconstruct the input under any circumstances. There are certainly reversible hash functions, but we do not consider such things in the scope of this book. For general-purpose usage, a minimally secure cryptographic hash algorithm should have a digest twice as large as a minimally secure symmetric key algorithm. MD5 and SHA1 are the most popular one-way cryptographic hash functions. MD5's digest length is only 128 bits, whereas SHA1's is 160 bits. For some uses, MD5's key length is suitable, and for others, it is risky. To be safe, we recommend using only cryptographic hash algorithms that yield 160-bit digests or larger, unless you need to support legacy algorithms. In addition, MD5 is widely considered "nearly broken" due to some cryptographic weaknesses in part of the algorithm. Therefore, we recommend that you avoid using MD5 in any new applications. Cryptographic hash functions have been put to many uses. They are frequently used as part of a password storage solution. In such circumstances, logins are checked by running the hash function over the password and some additional data, and checking it against a stored value. That way, the server doesn't have to store the actual password, so a well-chosen password will be safe even if an attacker manages to get a hold of the password database. Another thing people like to do with cryptographic hashes is to release them alongside a software release. For example, OpenSSL might be released alongside a MD5 checksum of the archive. When you download the archive, you can also download the checksum. Then you can compute the checksum over the archive and see if the computed checksum matches the downloaded checksum. You might hope that if the two checksums match, then you securely downloaded the actual released file, and did not get some modified version with a Trojan horse in it. Unfortunately, that isn't the case, because there is no secret involved. An attacker can replace the archive with a modified version, and replace the checksum with a valid value. This is possible because the message digest algorithm is public, and there is no secret information input to it. If you share a secret key with the software distributor, then the distributor could combine the archive with the secret key to produce a message digest that an attacker shouldn't be able to forge, since he wouldn't have the secret. Schemes for using keyed hashes, i.e., hashes involving a secret key, are called Message Authentication Codes (MACs). MACs are often used to provide message

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8 integrity for general-purpose data transfer, whether encrypted or not. Indeed, SSL uses MACs for this purpose. The most widely used MAC, and the only one currently supported in SSL and in OpenSSL, is HMAC. HMAC can be used with any message digest algorithm. 1.1.2.4 Digital signatures For many applications, MACs are not very useful, because they require agreeing on a shared secret. It would be nice to be able to authenticate messages without needing to share a secret. Public key cryptography makes this possible. If Alice signs a message with her secret signing key, then anyone can use her public key to verify that she signed the message. RSA provides for digital signing. Essentially, the public key and private key are interchangeable. If Alice encrypts a message with her private key, anyone can decrypt it. If Alice didn't encrypt the message, using her public key to decrypt the message would result in garbage. There is also a popular scheme called DSA (the Digital Signature Algorithm), which the SSL protocol and the OpenSSL library both support. Much like public key encryption, digital signatures are very slow. To speed things up, the algorithm generally doesn't operate on the entire message to be signed. Instead, the message is cryptographically hashed, and then the hash of the message is signed. Nonetheless, signature schemes are still expensive. For this reason, MACs are preferable if any sort of secure key exchange has taken place. One place where digital signatures are widely used is in certificate management. If Alice is willing to validate Bob's certificate, she can sign it with her private key. Once she's done that, Bob can attach her signature to his certificate. Now, let's say he gives the certificate to Charlie, and Charlie does not know that Bob actually gave him the certificate, but he would believe Alice if she told him the certificate belonged to Bob. In this case, Charlie can validate Alice's signature, thereby demonstrating that the certificate does indeed belong to Bob. Since digital signatures are a form of public key cryptography, you should be sure to use key lengths of 1,024 bits or higher to ensure security. 1.2 Overview of SSL SSL is currently the most widely deployed security protocol. It is the security protocol behind secure HTTP (HTTPS), and thus is responsible for the little lock in the corner of your web browser. SSL is capable of securing any protocol that works over TCP. An SSL transaction (see Figure 1-3) starts with the client sending a handshake to the server. In the server's response, it sends its certificate. As previously mentioned, a certificate is a piece of data that includes a public key associated with the server and other interesting information, such as the owner of the certificate, its expiration date, and the fully qualified domain name[2] associated with the server. [2] By fully qualified, we mean that the server's hostname is written out in a full, unambiguous manner that includes specifying the top-level domain. For example, if our web server is named "www", and our corporate domain is "securesw.com", then the fully qualified domain name for that host is "www.securesw.com". No abbreviation of this name would be considered fully qualified. Figure 1-3. An overview of direct communication in SSL