One More Turn, Less Regret: A Regret-Based Multi-Turn Benchmark for LLMs' Clarification Policies

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.

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.

User queries are often underspecified and may admit multiple valid interpretations. Rather than silently making assumptions about the user's intent, a helpful assistant should surface such ambiguity by asking a clarifying question. Doing so requires two abilities: recognizing that a query is ambiguous, and acting on that recognition by seeking clarification instead of answering directly. To study these abilities, we evaluate models on ambiguous, unambiguous, and disambiguated questions in three settings: standard question answering, explicit ambiguity judgment, and behavioral analysis, where a judge model classifies responses as direct answers, refusals, or clarifying questions. We find a clear gap between recognition and behavior: models often identify ambiguity when explicitly asked to judge it, yet in the QA setting they overwhelmingly default to direct answers. Retrieved context further widens this gap by improving answerability while making models even less likely to ask clarifying questions.