When Should AI Agents Ask? Clarification Requests Under Limited Human Attention

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.

LLM agents can ask clarifying questions to complete tasks, but answering each question demands users' time and effort. Existing evaluations typically measure this burden by counting questions, treating necessary and avoidable questions equally. We propose an evaluation protocol that distinguishes how often agents ask from how well they ask. An interruption budget limits the number of questions, while a user-attention cost charges extra for questions that are hard to read or not worth asking, as rated by a human-validated LLM judge. Beyond question counts, this cost captures perceived effort: on conversation pairs with the same number of questions, human annotators agreed with the cost on which conversation required more effort 75% of the time. Across eight LLMs and four customer-service domains, limiting agents to one to three questions reduces user-attention cost by 36-73% while keeping 86-94% of the task reward they earn with unlimited questions. At the same budget, reviewing each question against the memory of users' earlier answers cuts attention cost by another 13% with little reward loss and yields more valuable questions. Models also differ sharply in how well they ask: at the same user-attention cost, the most efficient models gain more than twice as much reward from their questions as the others. These results show that asking less and asking better are distinct goals, and that evaluations of proactive agents should measure both.

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.