Asking What Matters: Reward-Driven Clarification for Software Engineering Tasks

Pluralistic alignment requires systems to adapt to diverse user values, communication styles, and contextual assumptions. We believe that a foundational prerequisite for such alignment enabling accurate preference elicitation from people when their intent is under-specified or ambiguous. We study the problem of preference elicitation in multi-turn question answering by decomposing the problem into two components: a \textbf{clarification policy}, which decides whether to ask a clarifying question or answer directly, and \textbf{post-clarification answering}, which produces the correct final answer once the missing information is provided. We show, using the PACIFIC benchmark, that supervised fine-tuning rapidly improves the clarification policy, however, final answer accuracy remains substantially lower even when the model takes the correct action. This gap indicates that understanding and correctly interpreting the user's response is the critical gap in multi-turn question-answering systems.

As Large Language Model (LLM) agents are increasingly deployed in open-ended domains like software engineering, they frequently encounter underspecified instructions that lack crucial context. While human developers naturally resolve underspecification by asking clarifying questions, current agents are largely optimized for autonomous execution. In this work, we systematically evaluate the clarification-seeking abilities of LLM agents on an underspecified variant of SWE-bench Verified. We propose an uncertainty-aware multi-agent scaffold that decouples underspecification detection from code execution. Across both proprietary and open-weight frontier LLMs, our scaffold achieves a 69.40% task resolve rate, significantly outperforming a standard single-agent setup and closing the performance gap with agents operating on fully specified instructions. Furthermore, we find that the multi-agent system exhibits well-calibrated information-seeking behavior, conserving queries on simple tasks while proactively seeking information on more complex issues. These findings indicate that current models can be turned into proactive collaborators, where agents independently recognize when to ask questions to elicit missing information in real-world, underspecified tasks.

Ambiguous user requests make clarification a sequential decision problem for conversational LLM assistants: they must decide whether to ask, what to ask, when to stop, and when to answer. We introduce RegretBench, a multi-turn benchmark that evaluates clarification as policy behavior rather than isolated question quality. RegretBench provides a hidden-intent formulation of ambiguity, supports free-form interaction grounded in semantic-state tracking, and introduces a regret-based objective that measures how much value a model loses relative to a reference clarification policy. Experiments on open-domain QA and product recommendation scenarios show that final success alone is insufficient, as models with similar accuracy can differ substantially in efficiency, robustness to user behaviors, and stopping decisions. By jointly measuring intent resolution, interaction cost, ineffective clarification, and regret, RegretBench reveals whether models clarify usefully and efficiently. Our results show that effective clarification requires more than plausible questions: models must ask the right question at the right time and stop once the user's intended meaning is clear.