# SIRAJ: Diverse and Efficient Red-Teaming for LLM Agents via Distilled Structured Reasoning

arXiv: https://arxiv.org/abs/2510.26037 · HTML: https://mlsanity.com/paper/2510.26037/

## Key facts

- Cited by 5 papers in the map (data through 14 Oct 2026).
- Placed in Reasoning for agents, planning and code, one of 17 directions in LLM reasoning.
- Builds on 22 of its 29 references that are in the map.
- First posted on arXiv 30 Oct 2025.

## Placed in

- LLM reasoning / [Reasoning for agents, planning and code](https://mlsanity.com/lr/reasoning-for-agents-planning-and-code/)
- LLM agents and tool use / [Agent threats, guardrails and governance](https://mlsanity.com/agents/agent-threats-guardrails-and-governance/)
- LLM safety and security / [Prompt injection and agent security](https://mlsanity.com/safety/prompt-injection-and-agent-security/)

## Builds on (most cited first, 22 of 22)

- [DeepSeekMath: Pushing the Limits of Mathematical Reasoning in Open Language Models](https://mlsanity.com/paper/2402.03300/) (2024)
- [Qwen3 Technical Report](https://mlsanity.com/paper/2505.09388/) (2025)
- [DeepSeek-R1: Incentivizing Reasoning Capability in LLMs via Reinforcement Learning](https://mlsanity.com/paper/2501.12948/) (2025)
- [Universal and Transferable Adversarial Attacks on Aligned Language Models](https://mlsanity.com/paper/2307.15043/) (2023)
- [ToolLLM: Facilitating Large Language Models to Master 16000+ Real-world APIs](https://mlsanity.com/paper/2307.16789/) (2023)
- [InjecAgent: Benchmarking Indirect Prompt Injections in Tool-Integrated Large Language Model Agents](https://mlsanity.com/paper/2403.02691/) (2024)
- [AgentHarm: A Benchmark for Measuring Harmfulness of LLM Agents](https://mlsanity.com/paper/2410.09024/) (2024)
- [Agent-SafetyBench: Evaluating the Safety of LLM Agents](https://mlsanity.com/paper/2412.14470/) (2024)
- [AutoDAN-Turbo: A Lifelong Agent for Strategy Self-Exploration to Jailbreak LLMs](https://mlsanity.com/paper/2410.05295/) (2024)
- [MART: Improving LLM Safety with Multi-round Automatic Red-Teaming](https://mlsanity.com/paper/2311.07689/) (2023)
- [AgentDojo: A Dynamic Environment to Evaluate Prompt Injection Attacks and Defenses for LLM Agents](https://mlsanity.com/paper/2406.13352/) (2024)
- [Attacking Vision-Language Computer Agents via Pop-ups](https://mlsanity.com/paper/2411.02391/) (2024)
- [SafeArena: Evaluating the Safety of Autonomous Web Agents](https://mlsanity.com/paper/2503.04957/) (2025)
- [OpenAgentSafety: A Comprehensive Framework for Evaluating Real-World AI Agent Safety](https://mlsanity.com/paper/2507.06134/) (2025)
- [AdvAgent: Controllable Blackbox Red-teaming on Web Agents](https://mlsanity.com/paper/2410.17401/) (2024)
- [AutoRedTeamer: Autonomous Red Teaming with Lifelong Attack Integration](https://mlsanity.com/paper/2503.15754/) (2025)
- [AgentVigil: Generic Black-Box Red-teaming for Indirect Prompt Injection against LLM Agents](https://mlsanity.com/paper/2505.05849/) (2025)
- [RiOSWorld: Benchmarking the Risk of Multimodal Computer-Use Agents](https://mlsanity.com/paper/2506.00618/) (2025)
- [Jailbreak-R1: Exploring the Jailbreak Capabilities of LLMs via Reinforcement Learning](https://mlsanity.com/paper/2506.00782/) (2025)
- [Diverse and Effective Red Teaming with Auto-generated Rewards and Multi-step Reinforcement Learning](https://mlsanity.com/paper/2412.18693/) (2024)
- [UDora: A Unified Red Teaming Framework against LLM Agents by Dynamically Hijacking Their Own Reasoning](https://mlsanity.com/paper/2503.01908/) (2025)
- [Auto-RT: Automatic Jailbreak Strategy Exploration for Red-Teaming Large Language Models](https://mlsanity.com/paper/2501.01830/) (2025)

## Built on by (most cited first, 5 of 5)

- [SafePro: Evaluating the Safety of Professional-Level AI Agents](https://mlsanity.com/paper/2601.06663/) (2026)
- [T-MAP: Red-Teaming LLM Agents with Trajectory-aware Evolutionary Search](https://mlsanity.com/paper/2603.22341/) (2026)
- [Who Tests the Testers? Systematic Enumeration and Coverage Audit of LLM Agent Tool Call Safety](https://mlsanity.com/paper/2603.18245/) (2026)
- [PI-Hunter: Automated Red-Teaming for Exposing and Localizing Prompt Injections](https://mlsanity.com/paper/2606.12737/) (2026)
- [Attack Success Rate Is Not a Number: On Measurement Validity in Agentic AI Security Evaluation](https://mlsanity.com/paper/2609.25173/) (2026)

## Abstract (arXiv)

The ability of LLM agents to plan and invoke tools exposes them to new safety risks, making a comprehensive red-teaming system crucial for discovering vulnerabilities and ensuring their safe deployment. We present SIRAJ: a generic red-teaming framework for arbitrary black-box LLM agents. We employ a dynamic two-step process that starts with an agent definition and generates diverse seed test cases that cover various risk outcomes, tool-use trajectories, and risk sources. Then, it iteratively constructs and refines model-based adversarial attacks based on the execution trajectories of former attempts. To optimize the red-teaming cost, we present a model distillation approach that leverages structured forms of a teacher model's reasoning to train smaller models that are equally effective. Across diverse evaluation agent settings, our seed test case generation approach yields 2 -- 2.5x boost to the coverage of risk outcomes and tool-calling trajectories. Our distilled 8B red-teamer model improves attack success rate by 100%, surpassing the 671B Deepseek-R1 model. Our ablations and analyses validate the effectiveness of the iterative framework, structured reasoning, and the generalization of our red-teamer models.