TLS/HTTPS Security for Web Developers

Why This Course is for You

• Understand threats and attacks against encryption
• Identify real risks that apply to your systems
• Deploy servers with strong private keys and valid certificates
• Deploy TLS configurations with strong encryption and forward secrecy
• Understand higher-level attacks against web applications
• Use the latest defence technologies, such as HSTS, CSP, and HPKP
• Learn about key PKI standards and formats
• Understand where practice differs from theory
• Analyze certificate lifecycle in detail
• Evaluate PKI weaknesses and how they affect you
• Deploy robust protection using public key pinning
• Learn about what's coming in the future

Course Outline

On day 1, we’ll focus on what you need in your daily work to deliver best security, availability and performance. And you will learn how to get an A+ on SSL Labs! On day 2, we will start with the basics and the theory, then discuss how the PKI is implemented in the real world, and finish with a practical example of a realistic private certification authority.

Day 1: The Best TLS Training in the World

1. Introduction

• The need for network encryption
• Understanding encrypted communication
• The role of public key infrastructure (PKI)
• SSL/TLS and Internet PKI threat model

2. Keys and certificates

• RSA and ECDSA: selecting key algorithm and size
• Certificate hostnames and lifetime
• Practical work:
  • Private key generation
  • Certificate Signing Request (CSR) generation
  • Self-signed certificates
  • Obtaining valid certificates from Let’s Encrypt
• Sidebar: Revocation

3. Protocols and cipher suites

• Protocol security
• Key exchange strength
• Forward security
• Cipher suite configuration
• Practical work:
  • Secure web server configuration
  • Server testing using SSL Labs
• Sidebar: Server Name indication (SNI)
• Sidebar: Performance considerations

4. HTTPS topics

• Man in the middle attacks
• Mixed content
• Cookie security
• CRIME: Information leakage via compression
• HTTP Strict Transport Security
• Content Security Policy
• HTTP Public Key Pinning
• Practical work:
  • Deploying HSTS to deploy robust encryption
  • Deploying CSP to deal with mixed content

5. Putting it all together: Getting A+ in SSL Labs

Day 2: Internet PKI in Depth

1. Introduction

2. Standards

• X.509 certificates
• Certificate chains
• Name constraints
• Trust path building
• Validation process

3. Internet PKI

• Certification Authorities
• Relying parties
• Certificate types (DV, EV, OV)
• Certificate lifecycle (validation, issuance, and revocation)
• CA/B Forum and its standards
• Weaknesses
• History of attacks

4. Revocation

• CRL
• OCSP
• OCSP stapling
• CRLsets and OneCRL
• Short-lived certificates

5. Defenses

• Certification Authority Authorization (CAA)
• Public Key Pinning
  • Static pinning
  • HPKP
  • DNSSEC/DANE

6. Certificate Transparency

7. PKI ecosystem monitoring

• SSL Pulse
• Censys
• crt.sh

8. Project: Building and deploying a realistic private CA

We will also provide you with many additional exercises that you can work on in your own time. You'll be able to ask us for help via email. And if you're already familiar with the basics, we'll challenge you with some of the advanced exercises on the day.

Computer setup:

Attendees will need to bring a computer with the following software installed:

• Windows users need to download and install PuTTY (link) and
• Mac users will not need to install anything.