HTTPs/TLS Attacks

HTTPs/TLS Attacks  Medium

This module covers details on Transport Layer Security (TLS) and how it helps to make HTTP secure with the widely used HTTPS. That includes how TLS works, how TLS sessions are established, common TLS misconfigurations, as well as famous attacks on TLS. We will discuss how to identify, exploit, and prevent TLS attacks.

Created by vautia

To start this course Sign Up!


Transport Layer Security (TLS) is the standard protocol that is responsible for providing secure communication over the internet, including securing the unencrypted HTTP protocol to form HTTPS. As such it is used to secure a wide variety of services and applications. Therefore, vulnerabilities and misconfigurations in TLS can have catastrophic consequences. This module covers basics about the inner workings of TLS, as well as famous TLS attacks and common misconfigurations.

In more detail, this module covers the following:

  • Introduction to HTTPS/TLS
    • What is TLS and how does it relate to HTTPS?
    • Theoretical background knowledge about public key infrastructure (PKI)
    • Overview of the TLS 1.2 handshake and how TLS sessions are established
    • Overview of the TLS 1.3 handshake
  • Padding Oracle Attacks
    • What are padding oracles?
    • How to identify padding oracles
    • How to exploit padding oracles
    • What is a Bleichenbacher attack?
  • TLS Compression
    • Introduction to TLS compression
    • Attacks on TLS compression
  • Heartbleed Bug
    • What is the Heartbleed bug?
    • How to identify & exploit the Heartbleed bug
  • Misc Attacks
    • What is SSL Stripping?
    • How can we prevent SSL Stripping?
    • Overview of cryptographic attacks against TLS
    • What are Downgrade attacks?
  • TLS Best Practices
    • What are best practices for TLS servers?
    • How can we test the TLS configuration of TLS servers?

This module is broken into sections with accompanying hands-on exercises to practice each of the tactics and techniques we cover. The module ends with a practical hands-on skills assessment to gauge your understanding of the various topic areas.

You can start and stop the module at any time and pick up where you left off. There is no time limit or "grading," but you must complete all of the exercises and the skills assessment to receive the maximum number of cubes and have this module marked as complete in any paths you have chosen.

As you work through the module, you will see example commands and command output for the various topics introduced. It is worth reproducing as many of these examples as possible to reinforce further the concepts presented in each section. You can do this in the PwnBox provided in the interactive sections or your virtual machine.


  • Introduction to HTTPs/TLS
  • Public Key Infrastructure
  • TLS 1.2 Handshake
  • TLS 1.3
  • Padding Oracles
  • Bleichenbacher & DROWN
  • Intro to Compression
  • Heartbleed Bug
  • SSL Stripping
  • Cryptographic Attacks
  • Downgrade Attacks
  • Testing TLS Configuration
  • Skills Assessment
To start this course Sign Up!