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.
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.
Dialogue failures in language models are usually framed as memory failures: context too long, summaries lossy, a constraint forgotten. We argue this misses a deeper problem: in many conversations the model does not forget, it commits too early. An ambiguous early turn collapses into a single hidden interpretation, and later clarification is filtered through that commitment. We call this early posterior collapse: unresolved user intent collapsing into a committed task state before ambiguity is resolved. We study it with controlled dialogue tasks in writing, planning, and coding using Gemini-2.5-Pro and Gemini-2.5-Flash. Across thousands of trials, the same information in different orders yields different outcomes, even when the final dialogue contains equivalent task-relevant information. This order effect suggests later clarification is treated as extra context rather than a corrective signal: it refines a stale task state without invalidating it. Coding tasks are especially vulnerable, suggesting early assumptions get embedded in structured artifacts such as interfaces and control flow. Standard prompting and memory strategies do not reliably help: summaries can collapse ambiguity, and chain-of-thought can reduce explicit wrong commitment in reasoning traces without improving final task success. These findings motivate uncertainty-preserving state management. If assistants cannot let go of early interpretations, robustness cannot rely on post hoc correction alone; it must keep ambiguous early turns from hardening into one task state. Assistants should hold tentative hypotheses while ambiguity remains, ask before executing when high-impact ambiguity persists, and rebuild from a revised state when later evidence invalidates an earlier reading. Rather than one prompting fix, we aim to redirect research for interactive LLMs from retaining more context toward preserving uncertainty.
Current LLM safety alignment techniques improve model robustness against adversarial attacks, but overlook whether and how LLMs can recover helpfulness when benign users clarify their intent. We introduce CarryOnBench, the first interactive benchmark that measures whether LLMs can revise their interpretation of user intent and recover utility, while remaining safe through multi-turn conversations. Starting from 398 seemingly harmful queries with benign underlying intents, we simulate 5,970 conversations by varying user follow-up sequences, evaluating 14 models on both intent-aligned utility and safety. CarryOnBench yields 1,866 different conversation flows of 4--12 turns, totaling 23,880 model responses. We design Ben-Util, a checklist-based metric that evaluates how well each model response fulfills the user's benign information need using atomic items. At turn one, models fulfill only 10.5--37.6% of the user's benign information need. When the same query includes the benign intent upfront, models fulfill 25.1--72.1%, confirming that models withhold information due to intent misinterpretation, not limited knowledge. With benign clarifications in multi-turn conversations, 13 of 14 models approach or exceed this single-turn baseline, yet recovery cost varies across models. We identify three failure modes invisible to single-turn evaluations: utility lock-in, where a model rarely updates despite clarification; unsafe recovery, where a model updates at disproportionate safety cost; and repetitive recovery, where a model recycles prior responses rather than providing new information. Moreover, conversations converge to similar harmfulness levels regardless of how conservative the model starts. These findings expose a gap that single-turn evaluations miss -- whether a model is appropriately cautious or simply unresponsive to clarified user intent.