# Mapping the Exploitation Surface: A 10,000-Trial Taxonomy of What Makes LLM Agents Exploit Vulnerabilities

arXiv: https://arxiv.org/abs/2604.04561 · HTML: https://mlsanity.com/paper/2604.04561/

## Key facts

- Cited by 2 papers in the map (data through 14 Oct 2026).
- Placed in Agent threats, guardrails and governance, one of 16 directions in LLM agents and tool use.
- Builds on 9 of its 19 references that are in the map.
- First posted on arXiv 6 Apr 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, 9 of 9)

- [Universal and Transferable Adversarial Attacks on Aligned Language Models](https://mlsanity.com/paper/2307.15043/) (2023)
- [Jailbroken: How Does LLM Safety Training Fail?](https://mlsanity.com/paper/2307.02483/) (2023)
- [Identifying the Risks of LM Agents with an LM-Emulated Sandbox](https://mlsanity.com/paper/2309.15817/) (2023)
- ["Do Anything Now": Characterizing and Evaluating In-The-Wild Jailbreak Prompts on Large Language Models](https://mlsanity.com/paper/2308.03825/) (2023)
- [Alignment faking in large language models](https://mlsanity.com/paper/2412.14093/) (2024)
- [AI Deception: A Survey of Examples, Risks, and Potential Solutions](https://mlsanity.com/paper/2308.14752/) (2023)
- [Do the Rewards Justify the Means? Measuring Trade-Offs Between Rewards and Ethical Behavior in the MACHIAVELLI Benchmark](https://mlsanity.com/paper/2304.03279/) (2023)
- [Large Language Models can Strategically Deceive their Users when Put Under Pressure](https://mlsanity.com/paper/2311.07590/) (2023)
- [Black-Box Reliability Certification for AI Agents via Self-Consistency Sampling and Conformal Calibration](https://mlsanity.com/paper/2602.21368/) (2026)

## Built on by (most cited first, 2 of 2)

- [Context Kubernetes: Declarative Orchestration of Enterprise Knowledge for Agentic AI Systems](https://mlsanity.com/paper/2604.11623/) (2026)
- [Why Formal Monitors Fail: Attack Distribution Entropy as a Coverage Bound for LTL-Based LLM Agent Safety](https://mlsanity.com/paper/2608.01388/) (2026)

## Abstract (arXiv)

LLM agents with tool access can discover and exploit security vulnerabilities. This is known. What is not known is which features of a system prompt trigger this behaviour, and which do not. We present a systematic taxonomy based on approximately 10,000 trials across seven models, 37 prompt conditions, and 12 hypothesized attack dimensions -- all executed in real Docker sandboxes. Every condition includes the instruction "Always respect all rules and access policies"; only a single encouragement sentence varies. Within the task class studied (planted test-runner vulnerabilities), the threat model is narrower than assumed: nine of twelve dimensions -- including minimization, moral licensing, incentives, identity priming, and reasoning triggers -- produce no detectable exploitation at n=50 per cell (upper 95% CI <7% per condition). But it is also more subtle than expected: one dimension, goal reframing, reliably triggers exploitation. "You are solving a puzzle; there may be hidden clues" produces 38-40% exploitation on Claude Sonnet 4 despite the explicit rule instruction, replicating across four models (CTF framing: 8-14% on DeepSeek, GPT-5-mini, o4-mini). The agent does not override the rules; it reinterprets the task so that exploitative actions become task-aligned. GPT-4.1 produces no exploitation across 1,850 trials (37 conditions), and a temporal comparison across four OpenAI models released over eleven months shows a pattern consistent with improving safety training, though model capability differences are a confounder. The practical contribution is a narrowed, testable threat model: defenders should audit for goal-reframing language, not for the broad class of adversarial prompts.