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Ask Early, Ask Late, Ask Right: When Does Clarification Timing Matter for Long-Horizon Agents?
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Forced-injection study measuring how the value of ground-truth clarification for underspecified long-horizon agent tasks varies with injection timing across goal, input, constraint, and context dimensions, plus a 300-session natural-ask analysis of when frontier models actually ask.
Problem
When instructions are incomplete, long-horizon agents must decide when to ask for clarification; prior work treats clarification as binary and does not measure how its value changes over the course of execution.
Approach
Inject ground-truth clarifications at controlled, oracle-calibrated trajectory points (10% to 90%) and measure pass@3 decay per information dimension, then compare to natural ask timing of frontier models to find timing gaps.
Key results
- Goal clarification at 10% of trajectory yields pass@3 0.78 on MCP-Atlas vs 0.40 no-clarification, falling to baseline by 70%.
- Input clarification retains value through roughly 50% of execution (0.46 at Inj-10 vs 0.33 NC on MCP-Atlas).
- No frontier model asks within the empirically optimal window; GPT-5.2 asks in 52% of sessions at mean 43%, Gemini 3 Flash never asks.
Surprising findings
- Deferring any clarification type past mid-trajectory degrades performance below never asking at all.
- Gemini 3 Flash never asks in 100 natural sessions, and GPT-5.2 over-asks yet achieves lower per-session success (3%) than Claude (11%).
Limitations
- Demand side only; does not address agents' ability to detect ambiguity and ask at the right time.
- Small per-cell sample sizes (n=5-31), with floor effects on TheAgentCompany.
- Forced injection disables ask_user while natural-ask enables it, creating a behavioral confound.
Experimental setup
Datasets: LHAW MCP-Atlas TheAgentCompany SWE-Bench Pro
Benchmarks: MCP-Atlas TheAgentCompany SWE-Bench Pro
Metrics: pass@3 wasted compute point of no return Kendall tau cross-model consistency ask rate mean ask timing
Baselines: no-clarification oracle prompt
Builds on: LHAW MCP-Atlas TheAgentCompany SWE-Bench Pro HumanEval pass@k
Closest papers by meaning
- Uncertainty-Aware Clarification in LLM Agents with Information Gain (ICML 2026 · similarity 0.90)
- Agentic Abstention: Do Agents Know When to Stop Instead of Act? (NeurIPS 2026 · similarity 0.88)
- AMA-Bench: Evaluating Long-Horizon Memory for Agentic Applications (ICML 2026 · similarity 0.87)
- ASPI: Seeking Ambiguity Clarification Amplifies Prompt Injection Vulnerability in LLM Agents (NeurIPS 2026 · similarity 0.86)
- Selective Critique for Cost-Aware LLM Agents in Long-Horizon Decision Making (NeurIPS 2026 · similarity 0.86)
- Learning CLI Agents with Structured Action Credit under Selective Observation (NeurIPS 2026 · similarity 0.86)
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