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Abstract
A recent area of increasing research is the use of Large Language Models
(LLMs) in penetration testing, which promises to reduce costs and thus allow
for higher frequency. We conduct a review of related work, identifying best
practices and common evaluation issues. We then present AutoPentest, an
application for performing black-box penetration tests with a high degree of
autonomy. AutoPentest is based on the LLM GPT-4o from OpenAI and the LLM agent
framework LangChain. It can perform complex multi-step tasks, augmented by
external tools and knowledge bases. We conduct a study on three
capture-the-flag style Hack The Box (HTB) machines, comparing our
implementation AutoPentest with the baseline approach of manually using the
ChatGPT-4o user interface. Both approaches are able to complete 15-25 % of the
subtasks on the HTB machines, with AutoPentest slightly outperforming ChatGPT.
We measure a total cost of \$96.20 US when using AutoPentest across all
experiments, while a one-month subscription to ChatGPT Plus costs \$20. The
results show that further implementation efforts and the use of more powerful
LLMs released in the future are likely to make this a viable part of
vulnerability management.