Release date: March 2015
Last update: March 2016
Language: English (94 pages)
Formats: PDF, EPUB, Online
A short book that covers the most frequently used OpenSSL features and commands, by Ivan Ristić
- Provides OpenSSL documentation that covers installation, configuration,
and key and certificate management
- Includes SSL/TLS Deployment Best Practices, a design and deployment guide
- Written by the author of SSL Labs and
the SSL/TLS configuration assessment tool
- Available in a variety of digital formats (PDF, EPUB); no DRM
OpenSSL Cookbook
is a free ebook built around two OpenSSL chapters from Bulletproof SSL and TLS,
a larger work that teaches how to deploy secure servers and web applications.
Preface
Chapter 1. OpenSSL
Getting Started
Determine OpenSSL Version and Configuration
Building OpenSSL
Examine Available Commands
Building a Trust Store
Key and Certificate Management
Key Generation
Creating Certificate Signing Requests
Creating CSRs from Existing Certificates
Unattended CSR Generation
Signing Your Own Certificates
Creating Certificates Valid for Multiple Hostnames
Examining Certificates
Key and Certificate Conversion
Configuration
Cipher suite selection
Performance
Creating a Private Certification Authority
Features and Limitations
Creating a Root CA
Creating a Subordinate CA
Chapter 2. Testing with OpenSSL
Connecting to SSL Services
Testing Protocols that Upgrade to SSL
Using Different Handshake Formats
Extracting Remote Certificates
Testing Protocol Support
Testing Cipher Suite Support
Testing Servers that Require SNI
Testing Session Reuse
Checking OCSP Revocation
Testing Renegotiation
Testing for the BEAST Vulnerability
Testing for Heartbleed
Appendix A: SSL/TLS Deployment Best Practices
Introduction
1. Private Key and Certificate
1.1. Use 2048-bit Private Keys
1.2. Protect Private Keys
1.3. Ensure Sufficient Hostname Coverage
1.4. Obtain Certificates from a Reliable CA
1.5. Use Strong Certificate Signature Algorithms
2. Configuration
2.1. Deploy with Valid Certificate Chains
2.2. Use Secure Protocols
2.3. Use Secure Cipher Suites
2.4. Control Cipher Suite Selection
2.5. Support Forward Secrecy
2.6. Disable Client-Initiated Renegotiation
2.7. Mitigate Known Problems
3. Performance
3.1. Do Not Use Too Much Security
3.2. Ensure That Session Resumption Works Correctly
3.3. Use Persistent Connections (HTTP)
3.4. Enable Caching of Public Resources (HTTP)
3.5. Use OCSP Stapling
4. Application Design (HTTP)
4.1. Encrypt 100% of Your Web Site
4.2. Avoid Mixed Content
4.3. Understand and Acknowledge Third-Party Trust
4.4. Secure Cookies
4.5. Deploy HTTP Strict Transport Security
4.6. Disable Caching of Sensitive Content
4.7. Ensure That There Are No Other Vulnerabilities
5. Validation
6. Advanced Topics
About the Author
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Ivan Ristić is a security researcher, engineer, and author, known especially for his
contributions to the web application firewall field and development of ModSecurity, an open source web application firewall,
and for his SSL/TLS and PKI research, tools and guides published on the SSL Labs web site.
He is the author of two books, Apache Security and
ModSecurity Handbook, which he publishes via Feisty Duck, his own platform
for continuous writing and publishing. Ivan is an active participant in the security community and you'll often find him speaking
at security conferences such as Black Hat, RSA, OWASP AppSec, and others. His latest project, Hardenize, is a security posture analysis service that makes security fun again.
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Ivan's SSL Work
Below are links to some of Ivan's SSL work:
Qualys SSL Test
Detailed SSL configuration test of any public SSL server. Click here to test yours.
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