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.
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.
A long-lived LLM agent, such as OpenClaw, earns its value by acting on a user's preferences and constraints across sessions, not just the current request. Yet today's agents keep what a user volunteers but rarely ask for what stays unspoken, leaving a proactivity gap in long-lived LLM agents: an agent cannot act on a preference it never obtained. As users delegate more of their affairs to agents, the impact of this gap grows. We isolate one concrete, controllable slice of this gap as Ask-to-Remember (ATR): the agent decides whether to ask now for a reusable user preference that the current task does not need but a later session with the same user will. ATR is hard even to evaluate: the right question is underdetermined and its payoff deferred to tasks that may never arise. ATRBench, to the best of our knowledge the first ATR benchmark, makes it measurable by fixing each user's preferences as hidden ground truth, so success demands asking, not recall. Across eight frontier LLM agents, defaults fall at least 62 points below an oracle handed the relevant preference, and prompting closes little of it. Diagnostics identify acquisition as the bottleneck. ATRBench surfaces this proactivity gap in current agents and offers a diagnostic testbed for closing it.
Large Language Model (LLM) agents often operate under underspecified user instructions, where latent uncertainty over user intent leads to erroneous tool actions. To address this challenge, we propose a goal-oriented clarification framework that aligns clarification behavior with ambiguity resolution. Central to our approach is the Information Gain Reward, a metric that quantifies the utility of clarification questions by measuring the Bayesian belief update towards the ground-truth goal induced by the clarification exchange. We train the clarifier (LLM) using this reward to optimize for high information gain, ensuring that clarifications effectively reduce uncertainty and improve task completion within the agent-tool-user environment. We validate our framework within a clarification-enhanced τ-Bench environment, conducting cross-agent evaluations across five heterogeneous backbones. Empirical results demonstrate that our method consistently improves the success rate by 3.7% over the no-clarification baseline, while adding only 0.3 total interaction steps on average.