# Evaluating Language Model Reasoning about Confidential Information

arXiv: https://arxiv.org/abs/2508.19980 · HTML: https://mlsanity.com/paper/2508.19980/

## Key facts

- Cited by 3 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 47 of its 51 references that are in the map.
- First posted on arXiv 27 Aug 2025.

## Placed in

- LLM reasoning / [Reasoning for agents, planning and code](https://mlsanity.com/lr/reasoning-for-agents-planning-and-code/)

## Builds on (most cited first, 30 of 47)

- [Language Models are Few-Shot Learners](https://mlsanity.com/paper/2005.14165/) (2020)
- [Training language models to follow instructions with human feedback](https://mlsanity.com/paper/2203.02155/) (2022)
- [Chain-of-Thought Prompting Elicits Reasoning in Large Language Models](https://mlsanity.com/paper/2201.11903/) (2022)
- [Qwen3 Technical Report](https://mlsanity.com/paper/2505.09388/) (2025)
- [Direct Preference Optimization: Your Language Model is Secretly a Reward Model](https://mlsanity.com/paper/2305.18290/) (2023)
- [DeepSeek-R1: Incentivizing Reasoning Capability in LLMs via Reinforcement Learning](https://mlsanity.com/paper/2501.12948/) (2025)
- [GPT-4o System Card](https://mlsanity.com/paper/2410.21276/) (2024)
- [Toolformer: Language Models Can Teach Themselves to Use Tools](https://mlsanity.com/paper/2302.04761/) (2023)
- [Let's Verify Step by Step](https://mlsanity.com/paper/2305.20050/) (2023)
- [Training a Helpful and Harmless Assistant with Reinforcement Learning from Human Feedback](https://mlsanity.com/paper/2204.05862/) (2022)
- [Universal and Transferable Adversarial Attacks on Aligned Language Models](https://mlsanity.com/paper/2307.15043/) (2023)
- [Constitutional AI: Harmlessness from AI Feedback](https://mlsanity.com/paper/2212.08073/) (2022)
- [Self-Instruct: Aligning Language Models with Self-Generated Instructions](https://mlsanity.com/paper/2212.10560/) (2022)
- [Scaling LLM Test-Time Compute Optimally can be More Effective than Scaling Model Parameters](https://mlsanity.com/paper/2408.03314/) (2024)
- [Large Language Models Encode Clinical Knowledge](https://mlsanity.com/paper/2212.13138/) (2022)
- [Jailbroken: How Does LLM Safety Training Fail?](https://mlsanity.com/paper/2307.02483/) (2023)
- [HarmBench: A Standardized Evaluation Framework for Automated Red Teaming and Robust Refusal](https://mlsanity.com/paper/2402.04249/) (2024)
- [Jailbreaking Black Box Large Language Models in Twenty Queries](https://mlsanity.com/paper/2310.08419/) (2023)
- [Instruction-Following Evaluation for Large Language Models](https://mlsanity.com/paper/2311.07911/) (2023)
- [Llama Guard: LLM-based Input-Output Safeguard for Human-AI Conversations](https://mlsanity.com/paper/2312.06674/) (2023)
- [OSWorld: Benchmarking Multimodal Agents for Open-Ended Tasks in Real Computer Environments](https://mlsanity.com/paper/2404.07972/) (2024)
- [STaR: Bootstrapping Reasoning With Reasoning](https://mlsanity.com/paper/2203.14465/) (2022)
- [Tree of Attacks: Jailbreaking Black-Box LLMs Automatically](https://mlsanity.com/paper/2312.02119/) (2023)
- [JailbreakBench: An Open Robustness Benchmark for Jailbreaking Large Language Models](https://mlsanity.com/paper/2404.01318/) (2024)
- [The Instruction Hierarchy: Training LLMs to Prioritize Privileged Instructions](https://mlsanity.com/paper/2404.13208/) (2024)
- [Jailbreaking Leading Safety-Aligned LLMs with Simple Adaptive Attacks](https://mlsanity.com/paper/2404.02151/) (2024)
- [Safety Alignment Should Be Made More Than Just a Few Tokens Deep](https://mlsanity.com/paper/2406.05946/) (2024)
- [SmoothLLM: Defending Large Language Models Against Jailbreaking Attacks](https://mlsanity.com/paper/2310.03684/) (2023)
- [Improving Alignment and Robustness with Circuit Breakers](https://mlsanity.com/paper/2406.04313/) (2024)
- [Deliberative Alignment: Reasoning Enables Safer Language Models](https://mlsanity.com/paper/2412.16339/) (2024)

## Built on by (most cited first, 3 of 3)

- [Agent Tools Orchestration Leaks More: Dataset, Benchmark, and Mitigation](https://mlsanity.com/paper/2512.16310/) (2025)
- [When Should We Introduce Safety Interventions During Pretraining?](https://mlsanity.com/paper/2601.07087/) (2026)
- [From Leaky Thoughts to Private Reasoning: Controlling What LRMs Say to Themselves](https://mlsanity.com/paper/2602.24210/) (2026)

## Abstract (arXiv)

As language models are increasingly deployed as autonomous agents in high-stakes settings, ensuring that they reliably follow user-defined rules has become a critical safety concern. To this end, we study whether language models exhibit contextual robustness, or the capability to adhere to context-dependent safety specifications. For this analysis, we develop a benchmark (PasswordEval) that measures whether language models can correctly determine when a user request is authorized (i.e., with a correct password). We find that current open- and closed-source models struggle with this seemingly simple task, and that, perhaps surprisingly, reasoning capabilities do not generally improve performance. In fact, we find that reasoning traces frequently leak confidential information, which calls into question whether reasoning traces should be exposed to users in such applications. We also scale the difficulty of our evaluation along multiple axes: (i) by adding adversarial user pressure through various jailbreaking strategies, and (ii) through longer multi-turn conversations where password verification is more challenging. Overall, our results suggest that current frontier models are not well-suited to handling confidential information, and that reasoning capabilities may need to be trained in a different manner to make them safer for release in high-stakes settings.