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Abstract
Capture-the-Flag (CTF) competitions play a central role in modern cybersecurity as a platform for training practitioners and evaluating offensive and defensive techniques derived from real-world vulnerabilities. Despite recent advances in large language models (LLMs), existing LLM-based agents remain ineffective on high-difficulty cryptographic CTF challenges, which require precise cryptanalytic knowledge, stable long-horizon reasoning, and disciplined interaction with specialized toolchains. Through a systematic exploratory study, we show that insufficient knowledge granularity, rather than model reasoning capacity, is a primary factor limiting successful cryptographic exploitation: coarse or abstracted external knowledge often fails to support correct attack modeling and implementation. Motivated by this observation, we propose KryptoPilot, an open-world knowledge-augmented LLM agent for automated cryptographic exploitation. KryptoPilot integrates dynamic open-world knowledge acquisition via a Deep Research pipeline, a persistent workspace for structured knowledge reuse, and a governance subsystem that stabilizes reasoning through behavioral constraints and cost-aware model routing. This design enables precise knowledge alignment while maintaining efficient reasoning across heterogeneous subtasks. We evaluate KryptoPilot on two established CTF benchmarks and in six real-world CTF competitions. KryptoPilot achieves a complete solve rate on InterCode-CTF, solves between 56 and 60 percent of cryptographic challenges on the NYU-CTF benchmark, and successfully solves 26 out of 33 cryptographic challenges in live competitions, including multiple earliest-solved and uniquely-solved instances. These results demonstrate the necessity of open-world, fine-grained knowledge augmentation and governed reasoning for scaling LLM-based agents to real-world cryptographic exploitation.