The Disruptive Impact of Large Language Models on Capture the Flag Competitions and the Path Toward Fair Play
Authors: Michael Macaulay, Harmony Bouabid, Guo Gen Ang, Sasha Shaw
Abstract
Capture the Flag (CTF) competitions are among cybersecurity's most effective training grounds, developing practical skill across cryptography, web exploitation, and binary exploitation. Large language models (LLMs) can now solve a growing share of challenges with minimal human input, raising urgent questions about fairness, the validity of rankings, and whether participation still delivers the learning that justifies the effort. This paper reports a mixed-methods study of LLM impact on modern CTFs, combining a synthesis of published benchmarks, including a recent government evaluation, case studies of live competition across three challenge categories, structured observation of the public channels where the community debates AI use, and semi-structured interviews with experienced players and organisers. We map the current human-machine capability boundary by category, showing that easy and intermediate challenges in cryptography, web, and binary exploitation are now reliably automated while narrower sub-categories continue to resist. We find that community disagreement about whether AI should be permitted is downstream of an undeclared prior question: what a competition is for. Against this backdrop we contribute a four-component safeguard framework, combining tiered competition divisions, LLM-resistant challenge design, telemetry used investigatively, and a draft community code of conduct, together with a decision tool that ties the combination of safeguards to a competition's declared purpose. The argument reaches beyond CTFs to any setting in cybersecurity where a demonstrated result is taken as evidence of an underlying ability.
Recent advances in Large Language Models (LLMs) have enabled agentic systems for complex, multi-step tasks; cybersecurity is emerging as a prominent application. To evaluate such agents, researchers widely adopt Capture The Flag (CTF) benchmarks. However, current CTF benchmarks reuse existing challenges, which exposes them to data contamination and potential cheating. Notably, we confirmed these issues in practice by integrating web search tools into an existing agent. To address these limitations, we present CTFusion, a streaming evaluation framework built on Live CTFs. To achieve this, CTFusion preserves per-agent independence under a single team account and reduces competition impact by forwarding only the first correct flag per challenge. Moreover, we implement CTFusion as a Model Context Protocol (MCP) server on the widely used CTFd platform, which offers broad applicability to diverse CTF events and agent types. Through experiments with three LLMs, two agents, and five Live CTFs, we demonstrate that existing CTF benchmarks can be unreliable in assessing LLM-based agents, while CTFusion can serve as a robust solution for evaluating cybersecurity agents. We release CTFusion as open source to foster future research in this area.
Large Language Model (LLM) agents are increasingly proposed for autonomous cybersecurity tasks, but their capabilities in realistic offensive settings remain poorly understood. We present DeepRed, an open-source benchmark for evaluating LLM-based agents on realistic Capture The Flag (CTF) challenges in isolated virtualized environments. DeepRed places an agent in a Kali attacker environment with terminal tools and optional web search, connected over a private network to a target challenge, and records full execution traces for analysis. To move beyond binary solved/unsolved outcomes, we introduce a partial-credit scoring method based on challenge-specific checkpoints derived from public writeups, together with an automated summarise-then-judge labelling pipeline for assigning checkpoint completion from logs. Using DeepRed, we benchmark ten commercially accessible LLMs on ten VM-based CTF challenges spanning different challenge categories. The results indicate that current agents remain limited: the best model achieves only 35% average checkpoint completion, performing strongest on common challenge types and weakest on tasks requiring non-standard discovery and longer-horizon adaptation.
Large Language Model (LLM) agents are increasingly proposed to automate offensive security tasks, with recent studies reporting near human-level success rates in Capture-the-Flag (CTF) challenges. We here revisit these results, providing a second look at these claims. We engineer different agent architectures of increasing complexity and modularity on 30 web-based CTFs challenges spanning 14 vulnerability classes. We instantiate these agents with multiple LLM backbones, and compare them with claude-code, a general-purpose agent that automatically determines its internal architecture. Our evaluation yields three main findings. First, claude-code achieves performance comparable to the engineered architectures (19/30 solved tasks), suggesting that general-purpose agents are strong baselines for offensive security tasks. Second, both our architectures and claude-code struggle in the same challenge categories, revealing persistent barriers that keep current agents below human-level capability. Third, by leveraging our manually designed architectures we can systematically measure the impact of additional components, finding that structured orchestration of specialized roles outperforms monolithic designs, improving run-to-run consistency, and reducing execution costs.