Clarification

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.

Interactive robot planning requires robots to infer and execute human intentions from natural language instructions that are often ambiguous, incomplete, or underspecified. Although large language models (LLMs) provide a powerful interface for clarification, relying on the generative model to drive an multi-turn conversation can introduce systematic failures. We propose a Bayesian framework that treats clarification as an active learning problem over grounded Signal Temporal Logic (STL) task specifications. Our method uses LLMs to initialize candidate formal specifications and translate informative contrasts into natural-language clarification questions, while Bayesian optimization maintains uncertainty estimation over user intent and selects queries that maximize information gain. After convergence, the inferred STL specification is passed to a formal planner to synthesize a verifiable robot trajectory. Across four simulated and real-world task domains, our approach generally achieves higher task satisfaction and requires fewer clarification rounds than LLM baselines, while helping smaller models close the performance gap against larger reasoning models.

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.

A key challenge in reliable LLM deployment is recognizing when uncertainty reflects irreducible variability in the task rather than limitations in the model's knowledge. In language tasks, a central source of such aleatoric uncertainty is input ambiguity or underspecification, where multiple interpretations remain plausible. Existing decomposition methods estimate aleatoric uncertainty by generating multiple clarifications of the input, querying the model for an answer under each clarification, and comparing the resulting answers. We argue that answers are not necessary for identifying ambiguity: they are often redundant, add avoidable cost, and can mislead through epistemic leakage. We support this claim theoretically, and propose a clarification-only approach that estimates this ambiguity-induced component directly from the space of plausible interpretations, without answers to the clarified inputs. Using ambiguity detection as an operational evaluation across three benchmarks, this direct approach improves AUROC (63.34 vs. 60.85), reduces computational cost by 4-26x in output tokens and 2.2-3.5x in API calls, and yields estimates with substantially lower correlation with epistemic uncertainty. Overall, our results suggest that ambiguity-induced aleatoric uncertainty is better estimated from the interpretation space than from the response space.

Large language models (LLMs) are increasingly used to formulate optimization models from natural-language problem descriptions, yet realistic operations research (OR) requests are often incomplete: missing objectives, constraints, or business rules can change the resulting mathematical program. Existing evaluations largely assume a complete specification and therefore overlook whether an agent knows when clarification is needed before modeling. We introduce OR-Clarify, a benchmark for pre-formulation clarification. Each task presents a partial public problem description, withholds structured hidden slots, and evaluates agents through bounded interaction with a simulated user. The benchmark supports both openended and choice-based clarification, and measures slot recovery, stopping behavior, silent assumptions, and interaction cost. We further propose Interactive Optimization (InterOPT), a two-stage framework that identifies unresolved formulation-critical gaps and uses them to guide whether to ask the next question or to stop. In our choice-based experiments, InterOPT substantially outperforms all baselines in exact slot recovery; in the open-ended setting, it remains competitive with strong prior methods. Together, OR-Clarify and InterOPT reframe OR assistance as a selective completeness decision: clarify when needed, stop when ready, and quantify what remains missing.

Large Language Models (LLMs) are increasingly deployed in interactive systems where understanding user intent precisely is paramount. A key capability for such systems is effective question clarification, especially when user queries are ambiguous or underspecified. This paper introduces a novel tri-agent framework for the robust evaluation of an LLM's ability to engage in clarifying dialogue. Our framework comprises three distinct LLM-based agents: (1) a Question Clarifying Agent (QCA), the system under evaluation, tasked with identifying ambiguities and posing clarifying questions; (2) a Respondent Agent (RA), designed to simulate human user responses, potentially including irrelevant or challenging replies; and (3) an Evaluator Agent (EA), an LLM-as-a-judge, which assesses the quality of the dialogue based on a comprehensive set of metrics. We detail a methodology for synthetic data generation in the supply chain domain as an example. We propose metrics evaluating ambiguity handling, question quality, dialogue efficiency, language appropriateness, and final intent alignment. We also briefly discuss the validation of the EA against human judgments. This work provides a structured approach to benchmark, validate, and improve the clarification capabilities of conversational LLM applications.

Spectroscopic structure elucidation is central to molecular analysis, but recent Large Language Model (LLM)-based methods mostly formulate it as direct spectrum-to-SMILES generation. Although this paradigm can leverage paired spectral data, it does not explicitly model the analytical workflow used by spectroscopists, such as diagnostic peak interpretation, fragment reasoning, formula constraints, and chemical consistency checking. In this paper, we introduce S3C-LLM, a skill-guided and code-grounded agentic LLM for spectrum-to-structure elucidation. Rather than directly predicting a molecule, S3C-LLM retrieves modality-specific spectroscopy skills, executes analysis code to instantiate these skills on the input spectra, and integrates the resulting peak-level evidence and formula constraints before generating SMILES. Specifically, we contribute a self-evolving spectroscopy skill library, a thinking-augmented skill-code trajectory construction pipeline, and a two-stage training strategy that teaches Qwen3-4B through supervised fine-tuning (SFT) followed by our proposed step-level reinforcement learning (RL). Experiments on diverse benchmarks show that S3C-LLM consistently outperforms current general LLMs and spectrum-specific models across spectra, while using less than 1/10th of SpectraLLM's training corpus.

In open-domain human-computer interaction scenarios, large language models (LLMs) frequently encounter user queries that are ambiguous or incomplete. In such cases, directly producing an answer often leads to overgeneralized, erroneous, or low-information responses. In contrast, asking clarifying questions can substantially improve interaction quality. However, existing approaches still rely heavily on manually annotated data or preference alignment to address two fundamental challenges: when clarification is necessary, and which aspect of the query should be clarified. This reliance incurs high annotation costs and limits generalization. To address these challenges, we propose CLAIM, an uncertainty-driven framework for active clarification learning in open-domain settings. CLAIM eliminates the need for explicit human preference annotations by quantifying query uncertainty through the entropy induced by answer disagreements across multiple models. This uncertainty signal is then used to construct high-quality synthetic data, enabling the training of a unified clarification decision model through a combination of supervised learning and reinforcement learning. Specifically, we propose an entropy-driven synthetic data generation pipeline that integrates entropy-based uncertainty estimation with semantic clustering and reasoning-based judgments, enabling reliable automatic annotation of clarification requirements. To train CLAIM, we formulate the clarification process as a structured decision generation problem and adopt a training paradigm that combines supervised fine-tuning (SFT) with group-relative policy optimization (GRPO). Experimental results demonstrate that CLAIM can learn stable and generalizable clarification strategies without relying on manually labeled data, offering a low-cost and robust solution for proactive understanding in real-world open-domain interactions with LLMs.

A natural language interface can be used to make cancer genomics databases easier to use, but even if a question is perfectly fluent, its scientific meaning can be ambiguous. We propose CLARA, a framework that represents a question as a typed scientific query specification, considers a few possible interpretations, executes them, and asks for clarification when the estimates diverge. CLARA was assessed on mutation-prevalence contrasts among eight TCGA PanCancer Atlas cohorts and a 30-gene panel. This benchmark consisted of 330 unique executable contrasts varying in mutation scope, assay denominator, and sample context; 115 contrasts were result-sensitive and 215 were result-stable, per the preregistered definition of relative divergence greater than 0.10 or absolute divergence greater than 5 percentage points. An independently implemented pandas execution engine perfectly replicated all 660 results from the SQLite engine. In a separate 120-question LLM-generated, manually vetted language stress test, CLARA recognized all 60 result-sensitive contrasts and needlessly clarified 13 of 60 stable contrasts (accuracy 89.2%, sensitivity/recall 100%, specificity 78.3%). Standalone machine learning had superior overall accuracy (97.5%) but missed one critical contrast. This demonstrates that downstream execution can distinguish consequential from inconsequential ambiguity and reveal an explicit trade-off between safety and burden.

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.

Rewriting inputs to improve frozen downstream models has become a common strategy in modern NLP pipelines. Prior work on incremental dialogue discourse parsing (DDP) shows that supervised clarification models can rewrite fragmentary or underspecified utterances, such as resolving ellipsis or references, to improve parsing accuracy. In this work, we revisit this idea under realistic deployment conditions, where no clarification supervision is available and the clarifier must rely on zero-shot prompting or feedback from a frozen parser. Across three Segmented Discourse Representation Theory (SDRT) datasets and multiple parsers, we find that last-utterance clarification is far less reliable than suggested by supervised settings. Parser-agnostic rewriting often introduces more regressions than repairs, as edits that enable fixes also disrupt discourse cues relied upon by the parser. A best-of-8 rewriting analysis further reveals a practical ceiling: a large fraction of errors are not repairable through input rewriting alone. A parser-aware clarifier trained with GRPO reduces regressions by up to 37% by learning conservative abstention, yet still fails to produce selectivity-aware clarifications that consistently improve parsing. Together, these findings recast clarification as a selective intervention problem. We identify rewritability prediction, deciding whether an utterance is repairable before intervention, as the key missing capability for input-side optimization of frozen discourse parsers, and a critical direction for improving agentic pipelines more broadly.

Recent position papers argue that the classical aleatoric/epistemic uncertainty framework is insufficient for interactive large language model (LLM) agents and call for underspecification-aware, decomposed, and communicable uncertainty representations that can unlock new agent capabilities such as proactive clarification seeking and shared mental-model building. Practical deployment constraints -- black-box APIs, interactive latency budgets, and the absence of labeled trajectories -- rule out logprob-based, multi-sampling, and training-based methods, leaving prompt-based estimation as the most viable family for surfacing such signals at deployment time. We answer this call with a simple prompt-based decomposition that separates action confidence from request uncertainty (u), enabling the agent to ask for clarification when the task specification is ambiguous. To evaluate it, we introduce two clarification-augmented benchmarks (WebShop-Clarification and ALFWorld-Clarification) in which 50% of tasks are deliberately underspecified, and systematically compare the proposed decomposition against ReAct+UE and Uncertainty-Aware Memory (UAM) across five LLM backbones (GPT-5.1, DeepSeek-v3.2-exp, GLM-4.7, Qwen3.5-35B, GPT-OSS-120B) on these variants together with the standard WebShop, ALFWorld, and REAL benchmarks for fault detection. Averaged across the five backbones, the proposed decomposition improves clarification F1 on ALFWorld-Clarification by 73% over ReAct+UE and by 36% over UAM, and leads clarification F1 on every backbone on WebShop-Clarification and on four of five backbones on ALFWorld-Clarification, indicating that the gains generalize beyond a single LLM.

In hierarchical reasoning, failures often originate at intermediate decision points where the agent commits to a wrong branch without recognizing that it lacks critical information. Rather than treating clarification as an external uncertainty trigger, we propose ACTION-RATING, a formulation that places it inside the agent's action space on a shared ordinal scale with navigation, so that asking competes directly with acting at every decision point and help-seeking becomes observable at intermediate states. Two structurally distinct information-seeking modes emerge from the agent's own ratings: mandatory (no viable branch) and opportunistic (residual uncertainty despite a leading candidate). On Harmonized Tariff Schedule classification (30,000-node taxonomy, three benchmarks, 9~LLMs across 4 families), we observe a regime shift from mandatory to opportunistic clarification, with Information-Seeking Effectiveness (ISE), a local diagnostic defined as the fraction of help interactions followed by a correct next navigation step (not a final-task metric), rising from 50% to 74%. Three diagnostic contrasts fail to reproduce this structure. A separability test shows that the information-seeking pattern (mode split, ISE ranking) persists when answer quality is degraded (-18.8% accuracy), supporting an empirical separation between where an agent seeks help and the quality of the help it receives. Under the controlled answer channel, accuracy gains reach +16.2% at 10-digit; we read this as an upper bound on what better localization could unlock, not a deployment estimate.

Large language models (LLMs) define a distribution over text, which can be viewed as a probabilistic representation of uncertainty: sampling K responses yields a belief state - responses a model deems plausible. Existing work exploits this representation for narrow tasks like either decoding or selective prediction, and often requires manual interventions, not controlling generation directly. We propose Belief-Augmented Generation (BAG): grounding LLMs in their own belief state via the prompt and letting them reason over these K samples to decide on and execute a conversational strategy: clarify, abstain, or answer. In a multi-turn ambiguous question answering (QA) setting, we find that LLMs by default rarely clarify or abstain, ignoring uncertainty about the input (aleatoric) or facts (epistemic). BAG improves QA accuracy across six models and yields strategy decisions more faithful to their belief state than prompt-only baselines. Disentangling when to clarify from when to abstain, however, remains challenging.

Cascaded Automatic Speech Recognition - Large Language Model (ASR-LLM) pipelines remain popular for industrial Spoken Dialogue Systems (SDS), primarily because their decoupled design ensures perceptual verifiability. However, cascaded systems suffer from error propagation, as transcription failures inevitably cascade to subsequent components, thereby degrading the final interaction quality. Although ASR confidence scores offer a simple filter for unreliable inputs, this approach is fundamentally limited because it typically fails to detect deletion errors or to distinguish between acoustic (inability to hear clearly) and linguistic (inability to understand) mismatches, both of which require targeted recovery strategies. In this paper, we propose a cause-aware error recovery paradigm that fundamentally rethinks robustness in SDS. Unlike traditional confidence filtering, we introduce a suite of small precision-focused detectors that exploit deep ASR latent representations to disentangle token-level errors into perception, comprehension, and deletion failures. This fine-grained diagnostic intelligence empowers the LLM to orchestrate targeted, multi-turn clarification strategies, effectively transforming ambiguous signals into seamless user interactions. Experimental results validate the precision of our approach, which more than doubles the recall on domain-shift errors (57.96% vs. 23.66%) compared to baselines. Crucially, this diagnostic precision yields up to a 31% reduction in WER and a 19% improvement on the downstream task across diverse accents, distortions, and domains.

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.

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.

Multimodal Large Language Models have advanced visual reasoning, yet a purely textual chain of thought remains a bottleneck for questions that require fine-grained focus or view transformations. The ''think with images'' paradigm narrows this gap, but existing approaches are either constrained by fixed predefined toolkits or produce noisy intermediate images from unified multimodal methods. We pursue a third option: using a dedicated image editing model and decouple it with an understanding model. However, off-the-shelf image editors fail as reasoning assistants with two complementary gaps: a language-side gap, where editors trained as passive instruction-followers cannot map an abstract question to an appropriate visual transformation, and a generation-side gap, where edit correctness degrades as reasoning depth grows. Guided by this analysis, we introduce ETCHR (Editing To Clarify and Harness Reasoning), a question-conditioned, reasoning-aware image editor decoupled from the downstream understanding model and trained with a two-stage recipe targeted at the two gaps: Reasoning Imitation via supervised fine-tuning on edit trajectories, followed by Reasoning Enhancement with VLM-derived rewards for edit correctness and downstream reasoning accuracy. Since the editor is decoupled, ETCHR plugs into different open- and closed-source MLLMs in a training-free manner. Across five task families (fine-grained perception, chart understanding, logic reasoning, jigsaw restoration, and 3D understanding), ETCHR raises average Pass@1 from 55.95 to 60.77 (+4.82) with Qwen3-VL-8B, from 65.08 to 70.55 (+5.47) with Gemini-3.1-Flash-Lite, and from 76.55 to 81.16 (+4.61) with the 1T-parameter MoE model Kimi K2.5.

Long-horizon AI agents execute complex workflows spanning hundreds of sequential actions, yet a single wrong assumption early on can cascade into irreversible errors. When instructions are incomplete, the agent must decide not only whether to ask for clarification but when, and no prior work measures how clarification value changes over the course of execution. We introduce a forced-injection framework that provides ground-truth clarifications at controlled points in the agent's trajectory across four information dimensions (goal, input, constraint, context), three agent benchmarks, and four frontier models (three per benchmark; one on a single benchmark only; 84 task variants; 6,000+ runs). Counter to the common intuition that "earlier is always better," we find that the value of clarification depends sharply on what information is missing: goal clarification loses nearly all value after 10% of execution (pass@3 drops from 0.78 to baseline), while input clarification retains value through roughly 50%. Deferring any clarification type past mid-trajectory degrades performance below never asking at all. Cross-model Kendall tau correlations (0.78-0.87 among models sharing identical task coverage; 0.34-0.67 across the full 4-model panel) confirm these timing profiles are substantially task-intrinsic. A complementary study of 300 unscripted sessions reveals that no current frontier model asks within the empirically optimal window, with strategies ranging from over-asking (52% of sessions) to never asking at all. These empirical demand curves provide the quantitative foundation that existing theoretical frameworks require but have lacked, and establish concrete design targets for timing-aware clarification policies. Code and data will be publicly released.

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.

Reinforcement fine-tuning improves the reasoning ability of large language models, but it can also encourage them to answer unanswerable queries by guessing or hallucinating missing information. Existing abstention methods either train models to produce generic refusals or encourage follow-up clarifications without verifying whether those clarifications identify the key missing information. We study queries that are clear in meaning but cannot be reliably resolved from the given information, and argue that a reliable model should not only abstain, but also explain what is missing. We propose a clarification-aware RLVR reward that, while rewarding correct answers on answerable queries, jointly optimizes explicit abstention and semantically aligned post-refusal clarification on unanswerable queries. Using this reward, we train Abstain-R1, a 3B model that improves abstention and clarification on unanswerable queries while preserving strong performance on answerable ones. Experiments on Abstain-Test, Abstain-QA, and SelfAware show that Abstain-R1 substantially improves over its base model and achieves unanswerable-query behavior competitive with larger systems including DeepSeek-R1, suggesting that calibrated abstention and clarification can be learned through verifiable rewards rather than emerging from scale alone.

Humans often specify tasks incompletely, so assistants must know when and how to ask clarifying questions. However, effective clarification remains challenging in software engineering tasks as not all missing information is equally valuable, and questions must target information users can realistically provide. We study clarification in real software engineering tasks by quantifying which types of information most affect task success and which questions elicit useful responses from simulated users. Using Shapley attribution and distributional comparisons, we identify two key properties of effective clarification: task relevance (which information predicts success) and user answerability (what users can realistically provide). We operationalize these properties as multi-stage reinforcement learning rewards to train CLARITI, an 8B-parameter clarification module, that matches GPT-5's resolution rate on underspecified issues while generating 41% fewer questions. Our results suggest that grounding reward design in empirical analysis of information impact and user answerability improves clarification efficiency.