SkillDRE: Dual-Stage Red-Team Evolution of Agent Skills via Pre-Execution and Runtime Feedback

Agent skills extend LLM agents with reusable instructions, tool interfaces, and executable code, and users increasingly install third-party skills from marketplaces, repositories, and community channels. Because a skill exposes both executable behavior and context-setting documentation, its deployment risk cannot be measured by single-shot audits or prompt-level red teams alone: a realistic attacker can use audit and runtime feedback to repeatedly rewrite the skill. We frame this risk as \emph{adaptive leakage} -- whether a budgeted attacker can iteratively revise a skill until it passes audit and produces verified runtime harm -- and present \ours{}, a grey-box self-evolving red-team framework for measuring it. Proteus searches a formalized five-axis skill-attack space. Each candidate is evaluated through a unified audit-sandbox-oracle pipeline that returns structured audit findings and runtime evidence to guide cross-round mutation. Beyond initial evasion, Proteus performs path expansion, which finds alternative implementations of successful attacks, and surface expansion, which transfers learned implementation patterns to new attack objectives beyond the original seed catalogue. Across eight phase-1 cells, Proteus reaches 40--90% Attack Success Rate at $5$ rounds (ASR@5) with positive learning-curve slopes on both evaluated auditors. Phase-2 path/surface expansion produces 438 jointly bypassing and lethal variants, with SkillVetter bypassed at $\geq 93\%$ in every cell and AI-Infra-Guard, the strongest public auditor we evaluate, still admitting up to 41.3% joint-success. These results show that current skill vetting substantially underestimates residual risk when evaluated against adaptive, feedback-driven attackers.

Automated red-teaming has produced a growing collection of attack strategies, yet they typically remain scattered across prompts and workflows, making them difficult to systematically integrate, reuse, and improve at scale. We introduce \textsc{JailbreakSkill}, a skill-centric framework for scaling automated red-teaming through reusable and continuously evolving attack capabilities. \textsc{JailbreakSkill} packages existing attack strategies into modular, agent-ready skills that can be directly reused and adaptively selected across tasks and target models. Beyond reuse, it closes the loop between attacking and learning: attack experience is used to diagnose, refine, combine, and discover new skills, which are added back to an ever-growing skill library. This evolution lifts macro-average ASR by 17.5 percentage points on AdvBench and 13.4 points on HarmBench, including a 48.6-point gain against GPT-5.4 on AdvBench, while yielding novel attack strategies such as reframing a direct request as an unfinished document-completion task. Several evolved skills also generalize to unseen prompts and target models without further adaptation. Our code is available at https://github.com/BattleWen/JailbreakSkill.

LLM-based agents are increasingly deployed in product-level execution harnesses, where jailbreaks can trigger harmful tool use and persistent state changes, creating greater risks than unsafe text generation alone. Existing automatic red-teaming methods often rely on fixed attacks, while recent agentic attackers coordinate multiple jailbreak tools and show stronger potential through trajectory-based retrieval. However, such retrieval can reuse misleading experiences due to retrieval bias and unclear tool credit, and full trajectories add context overhead while reducing interpretability. We propose RedEvoAgent, a black-box red-teaming agent that distills cross-case attack trajectories into a concise, human-readable attack skill. The attack skill adaptively evolves through tool-effectiveness profiling and Deciding-Tool Attribution for skill updates, and a validation ratchet that retains only updates improving validation performance. Experiments on multiple benchmarks, target models, and target execution harnesses show that RedEvoAgent outperforms fixed and agentic baselines, improves tool efficiency, and transfers across attacker models and target execution harnesses.