Introducing The New Web Application Red Teaming Learning Path

Take Your Pentesting From “Finding Bugs” to Full-Scale Exploitation

In modern security testing, finding vulnerabilities is no longer enough.Organisations don’t just need lengthy vulnerability reports, they need real, demonstrable attack paths. They need to know how vulnerabilities can be chained, abused, weaponised and escalated to full compromise to allow them to better prioritise where to focus their remediation efforts.

This is where web application pentesting often stalls. Many testers know how to discover issues, but struggle to move from identification to exploitation with confidence. The gap between “I found a bug” and “I owned the entire app” is wide and growing.

To bridge this gap, we built the Web Application Red Teaming Learning Path.

This path teaches you to think and operate like a modern attacker: automating tooling, bypassing controls, breaking crypto, chaining flaws, attacking LLM-based systems, and evading WAF protections. Every module is hands-on, scenario-driven, and focused on real attack techniques used today.

Below is a deep dive into each module and why these skills matter more than ever.

Module 1: Cryptographic Failures

Break the crypto that developers trust the most.

Cryptography is often treated as a “black box” that only specialists can break but real-world applications frequently implement it incorrectly. These mistakes open the door to powerful, practical attacks. In this module, you'll learn how attackers target weak crypto used in web applications, including:

• ECB & Padding Oracles to recover plaintext from encrypted data
• Insecure Randomness to predict keys or break authentication
• Length Extension Attacks to forge signatures and tamper with data

Through accessible walkthroughs and hands-on labs, you’ll break crypto protections. You’ll learn why small implementation mistakes lead to catastrophic failures and how attackers exploit them with minimal effort. By the end, you’ll understand not only how to exploit cryptographic weaknesses, but how to recognise them instantly during real engagements.

Module 2: Custom Tooling

Because off-the-shelf tools don’t always cut it.

Sophisticated applications require sophisticated exploitation workflows. When Burp Suite extensions or proxies don’t give you the control you need, you must build your own tools. This module teaches you how to develop targeted, reusable tooling using:

• Python for automation, session handling, and bypassing protections
• Burp Suite extensions to intercept, manipulate, and decode complex traffic
• Browser automation to exploit dynamic applications and bypass client-side controls

You’ll learn to script payloads, automate exploitation steps, manipulate encrypted traffic, and simulate real user interactions at scale. By the end, you’ll be able to create your own offensive toolkit the kind testers rely on during high-stakes real-world assessments.

Module 3: Chaining Vulnerabilities

Turn small bugs into full compromise.

Most real breaches don’t start with a critical vulnerability. They start with a small misconfiguration, a harmless-looking endpoint, or a low-impact flaw. This module teaches you how attackers think: holistically, creatively, and offensively.

You’ll learn how to:

• Identify small flaws with “chain potential”
• Build attack paths by linking multiple vulnerabilities together
• Map each weakness as a stepping stone to a larger objective
• Develop full exploit chains from discovery to compromise

Finally, you’ll apply what you’ve learned to advanced, realistic challenges that force you to think like a red teamer and build attack chains from scratch. By the end, you won’t just find bugs you’ll turn them into full attack scenarios.

Module 4: Bypassing WAFs

Defeat the security layer that thinks it’s stopping you.

Web Application Firewalls (WAFs) are meant to protect applications from malicious traffic but many testers struggle to exploit behind them. Understanding WAF behaviour is a major differentiator between intermediate and advanced attackers. In this module, you’ll learn how WAFs actually work, how they detect traffic, and most importantly, how to evade them. You’ll master techniques such as:

• Signature and pattern bypasses
• Parsing and normalisation evasion
• Protocol manipulation
• Exploiting outdated or misconfigured WAF rules

You’ll then apply these techniques in real-world lab challenges where you analyse, bypass, and exploit applications behind WAF protection. This module turns WAFs from a blocker into just another obstacle to step over.

Module 5: Attacking LLMs

Exploit the vulnerabilities of AI-driven applications.

LLM-powered applications are exploding in popularity and with them, a new class of vulnerabilities has emerged. Very few pentesters can test these systems properly, making LLM exploitation one of the most in-demand modern skills. This module covers practical attacks against LLM-integrated systems, including:

• Prompt Injection to leak secrets or trigger unauthorised actions
• Unsafe Output Handling to escalate control in downstream systems
• Model Poisoning to create persistent failures via tainted training data

Through hands-on labs and realistic scenarios, you’ll learn how small oversights in LLM inputs or outputs can turn into full attack chains. You’ll also build concise, real-world POCs and learn practical mitigation strategies. By the end, you'll understand how LLM-based systems break and how attackers exploit them.

Build the Skills That Modern Pentesters Actually Need

The Web Application Red Teaming Learning Path was designed for learners who:

• Already know the basics of web pentesting.
• Want to go deeper into exploitation.
• Want to build attack chains, bypass defences, and break real systems.
• Want to operate like modern red teamers, not just checklist testers.

If you want to move beyond detection and start mastering exploitation, this learning path gives you the tools, techniques, and mindset to do it.

Ready to level up your methodology?

The Web Application Red Teaming Learning Path is now live. Dive in, break things, learn rapidly, and take your pentesting to the next level.