# Mind the Gap: Time-of-Check to Time-of-Use Vulnerabilities in LLM-Enabled Agents

arXiv: https://arxiv.org/abs/2508.17155 · HTML: https://mlsanity.com/paper/2508.17155/

## 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 9 of its 26 references that are in the map.
- First posted on arXiv 23 Aug 2025.

## 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)

- [HarmBench: A Standardized Evaluation Framework for Automated Red Teaming and Robust Refusal](https://mlsanity.com/paper/2402.04249/) (2024)
- [Prompt Injection attack against LLM-integrated Applications](https://mlsanity.com/paper/2306.05499/) (2023)
- [Defeating Prompt Injections by Design](https://mlsanity.com/paper/2503.18813/) (2025)
- [PoisonedRAG: Knowledge Corruption Attacks to Retrieval-Augmented Generation of Large Language Models](https://mlsanity.com/paper/2402.07867/) (2024)
- [Progent: Securing AI Agents with Privilege Control](https://mlsanity.com/paper/2504.11703/) (2025)
- [LlamaFirewall: An open source guardrail system for building secure AI agents](https://mlsanity.com/paper/2505.03574/) (2025)
- [AGrail: A Lifelong Agent Guardrail with Effective and Adaptive Safety Detection](https://mlsanity.com/paper/2502.11448/) (2025)
- [Prompt Flow Integrity to Prevent Privilege Escalation in LLM Agents](https://mlsanity.com/paper/2503.15547/) (2025)
- [An LLM-Tool Compiler for Fused Parallel Function Calling](https://mlsanity.com/paper/2405.17438/) (2024)

## Abstract (arXiv)

Large Language Model (LLM)-enabled agents are rapidly emerging across a wide range of applications, but their deployment introduces vulnerabilities with security implications. While prior work has examined prompt-based attacks (e.g., prompt injection) and data-oriented threats (e.g., data exfiltration), time-of-check to time-of-use (TOCTOU) remain largely unexplored in this context. TOCTOU arises when an agent validates external state (e.g., a file or API response) that is later modified before use, enabling practical attacks such as malicious configuration swaps or payload injection. In this work, we present the first study of TOCTOU vulnerabilities in LLM-enabled agents. We introduce TOCTOU-Bench, a benchmark with 66 realistic user tasks designed to evaluate this class of vulnerabilities. As countermeasures, we adapt detection and mitigation techniques from systems security to this setting and propose prompt rewriting, state integrity monitoring, and tool-fusing. Our study highlights challenges unique to agentic workflows, where we achieve up to 25% detection accuracy using automated detection methods, a 3% decrease in vulnerable plan generation, and a 95% reduction in the attack window. When combining all three approaches, we reduce the TOCTOU vulnerabilities from an executed trajectory from 12% to 8%. Our findings open a new research direction at the intersection of AI safety and systems security.