InformationalMay 20, 2023ChatGPT for Pen Testing (Pt. 1)

In recent times, the realm of cybersecurity has experienced remarkable progress with the integration of cutting-edge technologies, including Artificial Intelligence (AI). Among these advancements, ChatGPT has emerged as a ground-breaking AI model developed by OpenAI. While primarily designed to provide assistance across various domains, the potential of ChatGPT extends to the field of penetration testing—an essential process for evaluating and fortifying the security of computer systems. In part 1 of the “ChatGPT for Pen Testing” series, we will delve into the remarkable capabilities of ChatGPT in the context of penetration testing, exploring its inherent advantages, and limitations, and presenting real-world scenarios where its utilization can be both effective and efficient.

The Inner Workings of ChatGPT

ChatGPT represents the culmination of extensive research and development in the field of natural language processing. Built upon the GPT-3.5 architecture, this state-of-the-art model combines the power of deep learning with contextual understanding, enabling it to generate human-like responses to a wide array of queries. Its ability to comprehend and generate coherent text has positioned ChatGPT as a versatile tool for numerous applications, including penetration testing.

Leveraging ChatGPT in Penetration Testing

The integration of ChatGPT into the realm of penetration testing offers several advantages. Firstly, its natural language processing capabilities allow for seamless interaction with systems, simulating real-world scenarios where human input is required. Penetration testers can engage in dynamic conversations with ChatGPT, providing instructions or posing queries, and receive detailed responses that aid in identifying potential vulnerabilities.

Furthermore, ChatGPT can assist in automating certain aspects of the penetration testing process. By leveraging its contextual understanding, it can analyse vast amounts of data, including system logs, network traffic, and code snippets. This enables it to identify patterns, anomalies, and potential security weaknesses that may go unnoticed by traditional methods. By automating these initial stages of vulnerability detection, penetration testers can focus their efforts on more intricate and nuanced tasks.

Limitations and Ethical Considerations

While ChatGPT presents numerous advantages, it is essential to acknowledge its limitations and address ethical considerations. As with any AI model, ChatGPT is only as effective as the data it has been trained on. Therefore, it may exhibit biases or limitations in understanding certain contexts or providing accurate responses. This necessitates human oversight and critical evaluation of the model’s outputs.

Additionally, ethical guidelines must be adhered to when employing ChatGPT in penetration testing. Proper authorization and informed consent are crucial to ensure compliance with legal and ethical boundaries. Moreover, it is vital to protect the confidentiality and privacy of sensitive information during the testing process.

Although limited, we can still indirectly bypass this problem by changing the delivery of our sentences. For example, you can see in the screenshot below we indirectly asked ChatGPT to use GO language to create a DoS script:

Real-World Applications

The application of ChatGPT in penetration testing can extend to various real-world scenarios. For instance, it can be utilized to simulate social engineering attacks, allowing organizations to assess their susceptibility to phishing or impersonation attempts. ChatGPT can also aid in the analysis of complex web applications, automating the process of detecting vulnerabilities such as injection attacks or insecure direct object references.

Furthermore, in network security assessments, ChatGPT can assist in identifying potential weaknesses in firewall configurations or intrusion detection systems. By analysing network traffic logs and engaging in conversations that simulate network interactions, ChatGPT can provide insights into potential attack vectors and help enhance overall security defences.

For example, Although ChatGPT has some limitations and ethical considerations as we mentioned we can still convince ChatGPT to break the limitation and ethical considerations. In a real-life scenario, let’s consider crafting a phishing email to target an employee, whom we shall refer to as Mark, working at XYZ company. To execute this attack, we will assume the identity of Mark’s boss, Gus Firing, whom we will spoof:

Enhancing Pen Testing Assessments with ChatGPT

Integrating ChatGPT into penetration testing significantly enhances security assessments by complementing the capabilities of human testers. With its data analysis prowess, ChatGPT can swiftly sift through logs, system configurations, and code snippets, pinpointing potential vulnerabilities. This automation expedites the initial assessment stages, freeing up testers to dedicate more time and resources to in-depth analysis and creative problem-solving.

Moreover, ChatGPT’s natural language processing abilities enable it to engage in realistic conversations, mimicking real-world interactions. This enables comprehensive testing, including evaluating system defences against social engineering techniques like elicitation or pretexting. By leveraging ChatGPT’s conversational capabilities, penetration testers can assess an organization’s preparedness and response to various attack vectors.

Continuous Learning and Improvement

One of the remarkable advantages of ChatGPT is its ability to learn and improve over time. As new data is fed into the model, it adapts to emerging security trends, evolving attack techniques, and emerging vulnerabilities. This aspect of continuous learning makes ChatGPT an invaluable asset in the fast-paced world of cybersecurity.

By actively monitoring and updating the model with the latest security insights and threat intelligence, ChatGPT stays up to date with the ever-changing threat landscape. This adaptability ensures that penetration testers have access to the most relevant and accurate information during assessments. Regular retraining of ChatGPT with updated data sets ensures its effectiveness and maintains its value as a tool in the arsenal of security professionals.


The integration of ChatGPT into the field of penetration testing brings forth a new era of innovation. Its natural language processing capabilities, coupled with its ability to automate aspects of vulnerability detection, offer immense potential for enhancing the efficiency and effectiveness of security assessments. However, it is crucial to understand the limitations that come with any AI model. Human oversight and critical evaluation are essential to address biases and ensure the accuracy of responses. Ethical considerations must guide the use of ChatGPT, including obtaining proper authorization and protecting sensitive information. With responsible utilization, ChatGPT can serve as a powerful ally, revolutionizing the field of penetration testing and contributing to a more secure digital landscape. In the next blog, we will focus on how to actually utilize this technology to implement security in various web applications.

In part 2 of this series, we will utilize the full extent of this technology to provide general assistance during an engagement.

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Vivashu Rai

by Vivashu Rai

Security Consultant | Redfox Security