Learning to Clarify Underspecified Intents Under Limited Interaction

Current benchmarks for language models primarily evaluate execution on fully specified tasks. However, real user tasks are often ambiguous. Users arrive with incomplete, exploratory, or even inconsistent goals, requiring the assistant to first determine the intended task before carrying it out. We study this problem as task alignment: the ability to align with a user on their intended task. We introduce a general framework for converting specified tasks into underspecified interactions, formalized as a POMDP in which the model must infer a latent task from partial and evolving user intent. We validate our user simulator post hoc with a human user study. Across shopping, coding, and professional work settings, we find that while models often perform well once the task is specified, models still struggle with task alignment: current models act prematurely, interact ineffectively, and fail to resolve ambiguous requests. Models on average recover the user's intended task only 22-32% of the time under ambiguity. In a human study in the same setting, humans reach 48%, outperforming all evaluated models. We show that post-training with supervised fine-tuning and reinforcement learning improves task alignment, but models still lag behind humans in resolving uncertainty through interaction. Together, our results suggest that current models still lack key interaction abilities required for reliable agency.

Users of language-based assistive agents often make ambiguous requests. In response, an assistant can either directly act on its interpretation of the request --- risking misalignment with the user --- or ask a clarifying question. Which option is the most safe and helpful? A common approach is to ask questions that minimize uncertainty about the user's intent until a threshold is reached. However, this neglects the impact of uncertainty reduction on downstream performance, the costs of asking versus acting immediately, and the possibility that users may provide corrections without being asked. To navigate these trade-offs, we introduce Rational Enquiry via Value-of-Information Reasoning (REVOIR). REVOIR makes clarification decisions via inference-time reasoning about the value-of-information of a question, which captures the expected improvement in task reward due to the answer received. In two assistive tasks --- ambiguous question answering (CondAmbigQA) and preference-aligned household task planning (ADAPT) --- we show that REVOIR achieves greater success with fewer questions than approaches based on prompting, chain-of-thought, fine-tuning, or information gain, improving preference satisfaction on ADAPT by 13-15% over a fine-tuned clarification policy while requiring no training and asking five times fewer questions. Furthermore, when the assistant can receive cheap user corrections after acting, REVOIR naturally infers that asking questions is not always efficient, demonstrating the adaptivity of our approach. In contrast, we find that vanilla reasoning agents fail to adaptively clarify user requests, and request fewer clarifications as reasoning effort increases.

Instruction-tuned LLMs faced with underspecified queries often commit to a single interpretation rather than ask for clarification, producing confidently wrong answers. In our experiments, prompting alone is insufficient: models either ask for clarification on every query or ask vague questions that fail to recover the missing information. Addressing this failure requires learning two coupled skills: when to ask rather than answer and how to ask a question that recovers the disambiguating information. Existing recipes either address only one of these skills or require a separately trained critic. We propose CIGAsk, an RL recipe that teaches both skills through two complementary reward signals within a multi-turn GRPO loop. Counterfactual Information Gain (CIG) compares the gold-answer log-likelihood under a frozen reference model with and without the user response, providing per-turn credit that guides how to ask. The Asymmetric Ambiguity Bonus assigns a signed reward at the terminal token based on the gold ambiguity label, guiding when to ask. Across three clarification benchmarks spanning table, passage, and open-domain QA, CIGAsk-7B outperforms the strongest external baseline despite using a smaller backbone. It also transfers across datasets without per-dataset tuning while preserving single-turn QA performance on out-of-distribution benchmarks.