Generative AI agents, software systems powered by Large Language Models (LLMs), are emerging as a promising approach to automate cybersecurity tasks. Among the others, penetration testing is a challenging field due to the task complexity and the diverse strategies to simulate cyber-attacks. Despite growing interest and initial studies in automating penetration testing with generative agents, there remains a significant gap in the form of a comprehensive and standard framework for their evaluation and development. This paper introduces AutoPenBench, an open benchmark for evaluating generative agents in automated penetration testing. We present a comprehensive framework that includes 33 tasks, each representing a vulnerable system that the agent has to attack. Tasks are of increasing difficulty levels, including in-vitro and real-world scenarios. We assess the agent performance with generic and specific milestones that allow us to compare results in a standardised manner and understand the limits of the agent under test. We show the benefits of AutoPenBench by testing two agent architectures: a fully autonomous and a semi-autonomous supporting human interaction. We compare their performance and limitations. For example, the fully autonomous agent performs unsatisfactorily achieving a 21% Success Rate (SR) across the benchmark, solving 27% of the simple tasks and only one real-world task. In contrast, the assisted agent demonstrates substantial improvements, with 64% of SR. AutoPenBench allows us also to observe how different LLMs like GPT-4o or OpenAI o1 impact the ability of the agents to complete the tasks. We believe that our benchmark fills the gap with a standard and flexible framework to compare penetration testing agents on a common ground. We hope to extend AutoPenBench along with the research community by making it available under https://github.com/lucagioacchini/auto-pen-bench.

Password guessing approaches via deep learning have recently been investigated with significant breakthroughs in their ability to generate novel, realistic password candidates. In the present work we study a broad collection of deep learning and probabilistic based models in the light of password guessing: attention-based deep neural networks, autoencoding mechanisms and generative adversarial networks. We provide novel generative deep-learning models in terms of variational autoencoders exhibiting state-of-art sampling performance, yielding additional latent-space features such as interpolations and targeted sampling. Lastly, we perform a thorough empirical analysis in a unified controlled framework over well-known datasets (RockYou, LinkedIn, Youku, Zomato, Pwnd). Our results not only identify the most promising schemes driven by deep neural networks, but also illustrate the strengths of each approach in terms of generation variability and sample uniqueness.