CoRedSkill: Stealthy Skill Composition Attacks via AST-Guided Injection

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 JailbreakSkill, a skill-centric framework for scaling automated red-teaming through reusable and continuously evolving attack capabilities. 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.

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 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.

Agent skills package instructions, executable code, and task-specific resources into reusable artifacts that agents can improve using execution feedback. The same mechanism also enables attackers to evolve malicious skills, making them more effective and less detectable. However, a candidate skill may pass pre-execution scanning yet fail to realize its target under runtime defenses, while a revision that repairs execution may introduce new scanner findings. We introduce SkillDRE, a fully automated framework for evolving complete malicious skill packages through a dual-stage feedback loop. Given a benign task and its associated skills, SkillDRE autonomously constructs and validates a task-conditioned malicious objective and a verifiable judge rule. It then holds both fixed while evolving the skill implementation, with preservation of legitimate task capability. SkillDRE combines scanner-guided evolution with runtime-guided refinement informed by execution outcomes observed under runtime defense. Each runtime-guided revision returns to the pre-execution stage for rescanning and further optimization before re-execution, forming a cross-stage closed loop. Evaluated on SkillsBench across four victim models, SkillDRE achieves an average attack success rate of 45.28%, exceeding the strongest baseline by 40.3%, while its final submitted skills receive no SkillScan findings and largely preserve benign-task performance. These results show that two-stage defense feedback can serve as a useful learning signal for adaptive red teaming and that evaluating either defense stage in isolation can miss the resulting attack capability. Codes is available at https://github.com/whfeLingYu/SkillDRE