Capture the Flags: Family-Based Evaluation of Agentic LLMs via Semantics-Preserving Transformations

Agentic large language models (LLMs) are increasingly evaluated on cybersecurity tasks using capture-the-flag (CTF) benchmarks, yet existing pointwise benchmarks offer limited insight into agent robustness and generalisation across alternative versions of the source code. We introduce CTF challenge families, whereby a single CTF is used to generate a family of semantically-equivalent challenges via semantics-preserving program transformations, enabling controlled evaluation of robustness while keeping the underlying exploit strategy fixed. We present Evolve-CTF, a tool that generates CTF families from Python challenges using a range of transformations. Using Evolve-CTF to derive families from Cybench and Intercode challenges, we evaluate 13 agentic LLM configurations with tool access. We find that models are remarkably robust to renaming and code insertion, but that composed transformations and deeper obfuscation degrade performance by requiring more sophisticated tool use. Enabling explicit reasoning has little effect on success rates. Our work contributes a technique and tool for future LLM evaluations, and a large dataset characterising the capabilities of current state-of-the-art models in this domain.