Claude Code vs HackTheBox: Can AI Automate Pentesting?

Introduction

This tutorial explores how to automate penetration testing using AI, specifically by testing Claude Code on HackTheBox machines. It aims to demonstrate the capabilities of AI in cybersecurity, focusing on a fully automated approach without human intervention. By utilizing Kasm Workspaces, you can create a secure environment to run penetration tests safely.

Step 1: Setting Up Your Environment

Creating a secure testing environment is crucial for running penetration tests effectively. Follow these steps:

1. Use Kasm Workspaces:

   • Sign up for Kasm Workspaces.
   • Launch a Kali Linux desktop environment within Kasm. This ensures that your testing environment is isolated and does not affect your host system.

2. Configure Permissions:

   • Ensure that the Kali Linux instance has full command-execution permissions. This allows the AI to execute all necessary commands without restrictions.

Step 2: Understanding the Target Environment

Before running tests, familiarize yourself with the HackTheBox platform:

1. Sign Up for HackTheBox:

   • Create an account on HackTheBox if you haven't already. This platform offers various machines designed for security training and testing.

2. Select a Machine:

   • Choose a machine to test. HackTheBox has various challenges that simulate real-world vulnerabilities.

3. Learn About IDOR:

   • Understand the concept of Insecure Direct Object References (IDOR). This vulnerability is commonly tested in penetration testing. For a deeper understanding, refer to the IDOR explanation video here.

Step 3: Running Claude Code

Once your environment and targets are set, you can proceed to run Claude Code:

1. Launch Claude Code:

   • Open the terminal in your Kali Linux environment.
   • Start Claude Code with the appropriate command. (If specific commands were provided in the video, include them here.)

2. Execute Tests:

   • Allow Claude Code to perform its automated tests against the selected HackTheBox machine.
   • Monitor the output to see how effectively it identifies vulnerabilities.

3. Analyze Results:

   • Review the results provided by Claude Code. Check for any identified vulnerabilities and the methods used to exploit them.

Step 4: Evaluating AI Performance

After running the tests, assess the performance of Claude Code:

1. Compare Results:

   • Evaluate the findings from Claude Code against expected results or known vulnerabilities in the HackTheBox machine.

2. Identify Limitations:

   • Note any limitations or areas where the AI struggled to identify vulnerabilities. This assessment will help in understanding the current state of AI in penetration testing.

Conclusion

In this tutorial, we explored how to automate penetration testing using Claude Code within a secure environment on HackTheBox. Key steps included setting up Kasm Workspaces, understanding the target environment, running tests with AI, and evaluating its performance. As AI technology continues to evolve, it presents both opportunities and challenges in cybersecurity. For further exploration, consider trying different machines on HackTheBox or experimenting with other AI tools in penetration testing.