Traditional ethical hacking relies on skilled professionals and time-intensive command management, which limits its scalability and efficiency. To address these challenges, we introduce PenTest++, an AI-augmented system that integrates automation with generative AI (GenAI) to optimise ethical hacking workflows. Developed in a controlled virtual environment, PenTest++ streamlines critical penetration testing tasks, including reconnaissance, scanning, enumeration, exploitation, and documentation, while maintaining a modular and adaptable design. The system balances automation with human oversight, ensuring informed decision-making at key stages, and offers significant benefits such as enhanced efficiency, scalability, and adaptability. However, it also raises ethical considerations, including privacy concerns and the risks of AI-generated inaccuracies (hallucinations). This research underscores the potential of AI-driven systems like PenTest++ to complement human expertise in cybersecurity by automating routine tasks, enabling professionals to focus on strategic decision-making. By incorporating robust ethical safeguards and promoting ongoing refinement, PenTest++ demonstrates how AI can be responsibly harnessed to address operational and ethical challenges in the evolving cybersecurity landscape.

This study explores the application of generative AI (GenAI) within manual exploitation and privilege escalation tasks in Linux-based penetration testing environments, two areas critical to comprehensive cybersecurity assessments. Building on previous research into the role of GenAI in the ethical hacking lifecycle, this paper presents a hands-on experimental analysis conducted in a controlled virtual setup to evaluate the utility of GenAI in supporting these crucial, often manual, tasks. Our findings demonstrate that GenAI can streamline processes, such as identifying potential attack vectors and parsing complex outputs for sensitive data during privilege escalation. The study also identifies key benefits and challenges associated with GenAI, including enhanced efficiency and scalability, alongside ethical concerns related to data privacy, unintended discovery of vulnerabilities, and potential for misuse. This work contributes to the growing field of AI-assisted cybersecurity by emphasising the importance of human-AI collaboration, especially in contexts requiring careful decision-making, rather than the complete replacement of human input.

This technical report investigates the integration of generative AI (GenAI), specifically ChatGPT, into the practice of ethical hacking through a comprehensive experimental study and conceptual analysis. Conducted in a controlled virtual environment, the study evaluates GenAI's effectiveness across the key stages of penetration testing on Linux-based target machines operating within a virtual local area network (LAN), including reconnaissance, scanning and enumeration, gaining access, maintaining access, and covering tracks. The findings confirm that GenAI can significantly enhance and streamline the ethical hacking process while underscoring the importance of balanced human-AI collaboration rather than the complete replacement of human input. The report also critically examines potential risks such as misuse, data biases, hallucination, and over-reliance on AI. This research contributes to the ongoing discussion on the ethical use of AI in cybersecurity and highlights the need for continued innovation to strengthen security defences.