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Implementing SSL/TLS Using Cryptography and PKI

by Joshua Davies

January 2011

Intermediate to advanced

696 pages

16h 56m

English

Wiley

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Supplemental Web SitesRoadmap and Companion Source CodeOutline of the BookHow to Read This Book
What Are Secure Sockets?Insecure Communications: Understanding the HTTP ProtocolRoadmap for the Rest of This Book
Understanding Block Cipher Cryptography AlgorithmsUnderstanding Stream Cipher Algorithms
Understanding the Theory Behind the RSA AlgorithmPerforming Arbitrary Precision Binary Math to Implement Public-Key CryptographyEncryption and Decryption with RSAAchieving Perfect Forward Secrecy with Diffie-Hellman Key ExchangeGetting More Security per Key Bit: Elliptic Curve CryptographyMaking ECC Work with Whole Integers: Elliptic-Curve Cryptography over Fp
Using Message Digests to Create Secure Document Surrogates
Putting It Together: The Secure Channel ProtocolEncoding with ASN.1Developing an ASN.1 ParserManaging CertificatesOther Problems with Certificates
Implementing the TLS 1.0 Handshake (Client Perspective)Secure Data Transfer with TLSImplementing TLS ShutdownExamining HTTPS End-to-End Examples (TLS 1.0)Differences Between SSL 3.0 and TLS 1.0Differences Between TLS 1.0 and TLS 1.1
Implementing the TLS 1.0 Handshake from the Server's PerspectiveAvoiding Common Pitfalls When Adding HTTPS Support to a ServerWhen a Browser Displays Errors: Browser Trust Issues
Passing Additional Information with Client Hello ExtensionsSafely Reusing Key Material with Session ResumptionAvoiding Fixed Parameters with Ephemeral Key ExchangeVerifying Identity with Client AuthenticationDealing with Legacy Implementations: Exportable CiphersDiscarding Key Material Through Session Renegotiation
Supporting TLS 1.2 When You Use RSA for the Key ExchangeImpact to Diffie-Hellman Key ExchangeAdding Support for AEAD Mode CiphersWorking ECC Extensions into the TLS LibraryThe Current State of TLS 1.2
Adding the NTTPS Extension to the NTTP AlgorithmImplementing "Multi-hop" SMTP over TLS and Protecting Email Content with S/MIMESecuring Datagram TrafficSupporting SSL When Proxies Are InvolvedSSL with OpenSSL
The Decimal and Binary Numbering SystemsUnderstanding Binary Logical OperationsTwo's-Complement Representation of Negative NumbersBig-Endian versus Little-Endian Number Formats
Installing TCPDumpInstalling OpenSSL
Implementing the SSL Handshake

Content preview from Implementing SSL/TLS Using Cryptography and PKI

APPENDIX C

Understanding the Pitfalls of SSLv2

With all the elements of a secure connection — cryptography, authentication, secure key exchange and message authentication — it should be a simple matter to put it all together securely, right? Well, as it turns out, even when all the pieces are in place, it's surprisingly easy to get subtly wrong. Just ask the original Netscape engineers who released SSLv2. On paper, they did everything right, but the protocol was found to have subtle, but fatal flaws after it had been widely released. To the credit of the Netscape protocol designers, everybody else thought that they had gotten everything right the first time around as well. It wasn't until the protocol had been intensively studied in action that the chinks in the armor began to show.

Because SSLv2 was widely disseminated before it was found to be flawed, it's interesting to start by examining exactly how it worked, and then move on to see what's wrong with the protocol. SSL was specified fairly rigorously and submitted as an IETF draft (http://www.mozilla.org/projects/security/pki/nss/ssl/draft02.html), but its flaws were discovered before it was accepted, so it's never been officially blessed by the IETF. Although SSLv2 has been deprecated, there are pockets of support for it, so you can easily find the protocol details.

This appendix details an SSLv2 implementation similar to the TLS implementation presented in Chapter 6. I've assumed you're familiar with Chapter 6; I discuss ...