2025 EMNLP EMNLP 2025

Language Models Identify Ambiguities and Exploit Loopholes

Abstract

AbstractStudying the responses of large language models (LLMs) to loopholes presents a two-fold opportunity. First, it affords us a lens through which to examine ambiguity and pragmatics in LLMs, since exploiting a loophole requires identifying ambiguity and performing sophisticated pragmatic reasoning. Second, loopholes pose an interesting and novel alignment problem where the model is presented with conflicting goals and can exploit ambiguities to its own advantage. To address these questions, we design scenarios where LLMs are given a goal and an ambiguous user instruction in conflict with the goal, with scenarios covering scalar implicature, structural ambiguities, and power dynamics. We then measure different models’ abilities to exploit loopholes to satisfy their given goals as opposed to the goals of the user. We find that both closed-source and stronger open-source models can identify ambiguities and exploit their resulting loopholes, presenting a potential AI safety risk. Our analysis indicates that models which exploit loopholes explicitly identify and reason about both ambiguity and conflicting goals.

🌉 Interdisciplinary Bridge — Artificial Intelligence and Machine Learning and Natural Language Processing
🧭 Keyword Pioneer — loophole exploitation
🐝 Cross-Pollinator — Artificial Intelligence, Computer Science, Computer Vision, Data Science & Analytics, Deep Learning, Healthcare & Medicine, Interdisciplinary, Knowledge & Reasoning, Machine Learning, Mathematics & Optimization, Natural Language Processing, Reinforcement Learning, Robotics, Security & Privacy, Speech & Audio