# Agentic Security: A Systematization of Tools, Failure Modes, and Design Laws for LLM-Driven Penetration Testing

arXiv: https://arxiv.org/abs/2608.21423 · HTML: https://mlsanity.com/paper/2608.21423/

## Key facts

- No citing papers in the map yet (data through 14 Oct 2026).
- Placed in Agent threats, guardrails and governance, one of 16 directions in LLM agents and tool use.
- Builds on 17 of its 46 references that are in the map.
- First posted on arXiv 16 Aug 2026.

## Placed in

- LLM agents and tool use / [Agent threats, guardrails and governance](https://mlsanity.com/agents/agent-threats-guardrails-and-governance/)

## Builds on (most cited first, 17 of 17)

- [ReAct: Synergizing Reasoning and Acting in Language Models](https://mlsanity.com/paper/2210.03629/) (2022)
- [Toolformer: Language Models Can Teach Themselves to Use Tools](https://mlsanity.com/paper/2302.04761/) (2023)
- [Lost in the Middle: How Language Models Use Long Contexts](https://mlsanity.com/paper/2307.03172/) (2023)
- [AutoGen: Enabling Next-Gen LLM Applications via Multi-Agent Conversation](https://mlsanity.com/paper/2308.08155/) (2023)
- [Not what you've signed up for: Compromising Real-World LLM-Integrated Applications with Indirect Prompt Injection](https://mlsanity.com/paper/2302.12173/) (2023)
- [Jailbreaking Black Box Large Language Models in Twenty Queries](https://mlsanity.com/paper/2310.08419/) (2023)
- [RULER: What's the Real Context Size of Your Long-Context Language Models?](https://mlsanity.com/paper/2404.06654/) (2024)
- [Ignore Previous Prompt: Attack Techniques For Language Models](https://mlsanity.com/paper/2211.09527/) (2022)
- [Great, Now Write an Article About That: The Crescendo Multi-Turn LLM Jailbreak Attack](https://mlsanity.com/paper/2404.01833/) (2024)
- [Defeating Prompt Injections by Design](https://mlsanity.com/paper/2503.18813/) (2025)
- [Cybench: A Framework for Evaluating Cybersecurity Capabilities and Risks of Language Models](https://mlsanity.com/paper/2408.08926/) (2024)
- [LLM Agents can Autonomously Exploit One-day Vulnerabilities](https://mlsanity.com/paper/2404.08144/) (2024)
- [LLM Agents can Autonomously Hack Websites](https://mlsanity.com/paper/2402.06664/) (2024)
- [PentestGPT: An LLM-empowered Automatic Penetration Testing Tool](https://mlsanity.com/paper/2308.06782/) (2023)
- [AutoAttacker: A Large Language Model Guided System to Implement Automatic Cyber-attacks](https://mlsanity.com/paper/2403.01038/) (2024)
- [Getting pwn'd by AI: Penetration Testing with Large Language Models](https://mlsanity.com/paper/2308.00121/) (2023)
- [Design Patterns for Securing LLM Agents against Prompt Injections](https://mlsanity.com/paper/2506.08837/) (2025)

## Abstract (arXiv)

Agentic security uses large-language-model (LLM) agents to plan, dispatch, and interpret security tools. As these systems move from demonstrations to deployed products, practitioners repeatedly encounter the same operational failures. We systematize these failures through a hands-on evaluation of ten widely used static, dynamic, cloud, orchestration, and AI red-teaming tools for unattended pipelines. We introduce a four-dimensional Integration Friction Index that separates one-time engineering cost from recurring organisational, legal, and maintenance cost. We then derive quantitative regularities that explain recurring failure modes. Modelling an agentic security system as stochastic LLM policies wrapped by a deterministic mediator, we show that long-lived sessions lose resident evidence with phase count, while short-lived sub-agents extend the usable horizon according to the compression ratio between raw evidence and its summary. We show that a two-stage verdict cascade multiplies scorer likelihood ratios, but provides little benefit when scorer errors correlate. We show that treating unevaluable outcomes as attack failures biases downstream measurements toward evasive and severe responses. We formulate planner-versus-worker model routing as a knapsack problem and derive a closed-form execution cap for heavy-tailed tools, eta* = alpha v/c. Finally, we show why scope and budget enforcement cannot be delegated to system prompts: prompts do not constrain what actually executes. Inspectra, our implemented platform, serves as a worked instantiation, with mechanisms labelled shipped, partial, or planned, including those that did not work.