# Pigeonholing: how bad prompts hurt models, causing collapse and mistakes

arXiv: https://arxiv.org/abs/2606.24267 · HTML: https://mlsanity.com/paper/2606.24267/

## Key facts

- No citing papers in the map yet (data through 14 Oct 2026).
- Placed in Jailbreaking, one of 12 directions in LLM safety and security.
- Builds on 36 of its 59 references that are in the map.
- First posted on arXiv 23 Jun 2026.

## Placed in

- LLM safety and security / [Jailbreaking](https://mlsanity.com/safety/jailbreaking/)

## Builds on (most cited first, 30 of 36)

- [Language Models are Few-Shot Learners](https://mlsanity.com/paper/2005.14165/) (2020)
- [Proximal Policy Optimization Algorithms](https://mlsanity.com/paper/1707.06347/) (2017)
- [Direct Preference Optimization: Your Language Model is Secretly a Reward Model](https://mlsanity.com/paper/2305.18290/) (2023)
- [Think you have Solved Question Answering? Try ARC, the AI2 Reasoning Challenge](https://mlsanity.com/paper/1803.05457/) (2018)
- [Large Language Models are Zero-Shot Reasoners](https://mlsanity.com/paper/2205.11916/) (2022)
- [GPQA: A Graduate-Level Google-Proof Q&A Benchmark](https://mlsanity.com/paper/2311.12022/) (2023)
- [High-Dimensional Continuous Control Using Generalized Advantage Estimation](https://mlsanity.com/paper/1506.02438/) (2015)
- [LiveCodeBench: Holistic and Contamination Free Evaluation of Large Language Models for Code](https://mlsanity.com/paper/2403.07974/) (2024)
- [Gemma 2: Improving Open Language Models at a Practical Size](https://mlsanity.com/paper/2408.00118/) (2024)
- [MMLU-Pro: A More Robust and Challenging Multi-Task Language Understanding Benchmark](https://mlsanity.com/paper/2406.01574/) (2024)
- [Towards Understanding Sycophancy in Language Models](https://mlsanity.com/paper/2310.13548/) (2023)
- [Large Language Models Cannot Self-Correct Reasoning Yet](https://mlsanity.com/paper/2310.01798/) (2023)
- [How Johnny Can Persuade LLMs to Jailbreak Them: Rethinking Persuasion to Challenge AI Safety by Humanizing LLMs](https://mlsanity.com/paper/2401.06373/) (2024)
- [DecodingTrust: A Comprehensive Assessment of Trustworthiness in GPT Models](https://mlsanity.com/paper/2306.11698/) (2023)
- [LLMs Get Lost In Multi-Turn Conversation](https://mlsanity.com/paper/2505.06120/) (2025)
- [Larger language models do in-context learning differently](https://mlsanity.com/paper/2303.03846/) (2023)
- [Great, Now Write an Article About That: The Crescendo Multi-Turn LLM Jailbreak Attack](https://mlsanity.com/paper/2404.01833/) (2024)
- [Way Off-Policy Batch Deep Reinforcement Learning of Implicit Human Preferences in Dialog](https://mlsanity.com/paper/1907.00456/) (2019)
- [LiveBench: A Challenging, Contamination-Limited LLM Benchmark](https://mlsanity.com/paper/2406.19314/) (2024)
- [Can language models learn from explanations in context?](https://mlsanity.com/paper/2204.02329/) (2022)
- [Artificial Hivemind: The Open-Ended Homogeneity of Language Models (and Beyond)](https://mlsanity.com/paper/2510.22954/) (2025)
- [ELEPHANT: Measuring and understanding social sycophancy in LLMs](https://mlsanity.com/paper/2505.13995/) (2025)
- [X-Teaming: Multi-Turn Jailbreaks and Defenses with Adaptive Multi-Agents](https://mlsanity.com/paper/2504.13203/) (2025)
- [Are Emergent Abilities in Large Language Models just In-Context Learning?](https://mlsanity.com/paper/2309.01809/) (2023)
- [Measuring Sycophancy of Language Models in Multi-turn Dialogues](https://mlsanity.com/paper/2505.23840/) (2025)
- [Feedback Loops With Language Models Drive In-Context Reward Hacking](https://mlsanity.com/paper/2402.06627/) (2024)
- [Chain of Attack: a Semantic-Driven Contextual Multi-Turn attacker for LLM](https://mlsanity.com/paper/2405.05610/) (2024)
- [From Yes-Men to Truth-Tellers: Addressing Sycophancy in Large Language Models with Pinpoint Tuning](https://mlsanity.com/paper/2409.01658/) (2024)
- [SuperCorrect: Advancing Small LLM Reasoning with Thought Template Distillation and Self-Correction](https://mlsanity.com/paper/2410.09008/) (2024)
- [Cultivating Pluralism In Algorithmic Monoculture: The Community Alignment Dataset](https://mlsanity.com/paper/2507.09650/) (2025)

## Abstract (arXiv)

While in-context learning is generally shown to be effective in Large Language Models (LLMs), bad contexts can cause performance degradation and mode collapse, a phenomenon we call "pigeonholing." **Unintentionally bad** contexts can happen without malicious jailbreaking intents: For example, a user asks the model to justify an incorrect math theorem or fails to correct the model's buggy code. Specifically, we investigate ``pigeonholing" in two scenarios: (1) when the user suggests a solution, and (2) when the conversation context includes the assistant's previous (incorrect) responses. Our experiments across 10 verifiable and open-ended tasks with 10 different models show that pigeonholing manifests in several ways: (1) repeating the incorrect answers from context (leading to 38-40% performance drop), (2) converging on a narrow set of answers in coding and text generation without exploring alternatives, and (3) flipping stance on controversial topics to align with the user or the assistant's previous claims. We find that pigeonholing worsens almost monotonically with the number of conversation turns (performance drops by additional 14+% as repeated mistakes increase from 1 to 5), and pigeonholing-induced mode collapse can happen even when the provided example is correct. As a step toward mitigation, we propose RLVR with synthetic errors which improves models by 43-60% under bad contexts compared to vanilla RLVR baselines.