PentestGPT: How AI is Changing the Game in Penetration Testing

Penetration testing, or “pentesting”, has always been a key part of cybersecurity. It helps organisations find vulnerabilities before attackers do. However, traditional pentesting is time-consuming, requires deep expertise, and often comes with a price tag.

Let’s talk about PentestGPT, a new AI-powered tool that’s changing how both amateurs and professionals approach security testing.

What is PentestGPT?

PentestGPT is a ChatGPT-based tool designed to help security professionals conduct penetration tests more efficiently. It was developed to assist with tasks like vulnerability discovery, exploitation, and even report generation.

Built on OpenAI’s GPT models, PentestGPT uses natural language to communicate, which means testers can interact with it conversationally. This makes it especially helpful for junior pentesters or IT professionals who need some guidance through the process.

Why It Matters

Here’s why PentestGPT is getting attention in the security world:

• Speed: It can automate routine tasks and speed up reconnaissance and information gathering.
• Accessibility: It lowers the barrier to entry for those new to cybersecurity.
• Documentation: It helps generate clear, detailed reports, which are essential for audits and client communication.

According to a 2024 paper by Gelei Deng. Yi Liu et al. from the Nanyang Technological University, PentestGPT is “capable of automating a large portion of a typical penetration testing workflow while remaining human-in-the-loop.”

Real-World Example: Testing a Web App

Let’s say you’re testing a web application for vulnerabilities. Normally, you’d need to manually check for issues like SQL injection or broken authentication, as well as initial reconnaissance to figure out which ports are open (if any), which versions do the services run, etc.

With PentestGPT, you could do the following:

1. Use it to suggest an appropriate nmap scan (or similar recon tool) for your use-case.
2. Ask it to generate a list of common attack vectors for web apps.
3. Have it suggest payloads for testing input fields.
4. Use it to interpret responses from the application (like error messages or unusual behaviour).
5. Ask it to summarise findings in a professional report format.

For example, you might input:

“I’ve found a login page at /admin. Can you help me test it for SQL injection?”

PentestGPT could then suggest specific payloads like:

admin' OR '1'='1

What It Can (and Can’t) Do

PentestGPT isn’t a replacement for skilled penetration testers. It’s a tool, not a hacker-in-a-box.

It’s best used for:

• Scanning and enumeration
• Generating test cases and payloads
• Interpreting scan results
• Writing up findings in a report

But it has limitations:

• It can’t interact with systems in real time.
• It doesn’t replace human judgment or legal/ethical responsibility.
• It may need updates to keep up with evolving threats and tools.

As mentioned in the official GitHub repo’s Q&A, it uses GPT 4.0’s API, because of its better performance as a reasoning model (when compared to 3.5) and a lesser loss of context once your investigation gets deeper.

A (subjectively) very useful quality-of-life feature is that a PentestGPT session can be initialised via terminal, meaning that the pentesting process can be streamlined without having to switch back-and-forth between your browser and your terminal or code editor.

Caution and Ethics

Just like with any AI tool, how you use PentestGPT matters.

• In accordance with the white hat ethos, always have proper authorisation before testing a system, in case you aren’t testing something you built locally for your own purposes.
• You shouldn’t rely solely on AI and be sure to validate everything it suggests. It’s based on ChatGPT, and at the time of this writing (May 2025), ChatGPT is still known to make mistakes in judgement and possibilities once in a while.
• Lack of total optimisation — while PentestGPT will suggest an appropriate command when agreed with a course of action (for example, a nmap scan command), the generated command is not necessarily optimised for your use-case. For example, some of the flags and arguments might not be relevant for your needs and may even cause the scan to last for quite a bit longer than necessary. As always, human consideration and double-checking before running the commands is advised.
• Tunnel vision — when PentestGPT suggests several attack approaches, this doesn’t mean they are the only possible ones. We should always perform our own analysis of the system and use human intelligence to determine any potential attack vectors PentestGPT might have missed.
• Be transparent with clients or stakeholders when using AI in your pentesting process.

AI-assisted pentesting is powerful, but it still operates within ethical and legal boundaries, and its misuse could lead to serious consequences.

The Future of AI in Security

PentestGPT is just the beginning. We’re already seeing AI tools that can:

• Detect anomalies in real-time network traffic
• Automatically generate security policies
• Identify zero-day vulnerabilities using pattern analysis

That said, security is an ever-evolving field. As defenders use AI to get better, so will attackers. The ‘arms race’ continues, but tools like PentestGPT give ethical hackers a new edge.

Final Thoughts

PentestGPT isn’t here to replace human pentesting efforts, it’s here to help them work smarter.  Whether you’re an experienced penetration tester or just getting started in cybersecurity, it’s a tool worth exploring. Once again, it doesn’t do The Work for you, but it gives you a very good idea where to start, which path to take. Plus, it’s pretty good (most of the time) at handling the specifics.

By combining the deep knowledge of GPT with the structured logic of penetration testing, we’re stepping into a new era of intelligent, assisted security. And considering that we’re still in the earlier stages of LLM and general AI development, who knows where the limits will be?

If you have any questions, need assistance, or want to learn more about how PentestGPT can support your security efforts, feel free to reach out!