When and How Should an Agent Clarify? CIGAsk: Teaching LLMs to Clarify via Counterfactual Information Gain

Instruction-tuned LLMs faced with underspecified queries often commit to a single interpretation rather than ask for clarification, producing confidently wrong answers. In our experiments, prompting alone is insufficient: models either ask for clarification on every query or ask vague questions that fail to recover the missing information. Addressing this failure requires learning two coupled skills: when to ask rather than answer and how to ask a question that recovers the disambiguating information. Existing recipes either address only one of these skills or require a separately trained critic. We propose CIGAsk, an RL recipe that teaches both skills through two complementary reward signals within a multi-turn GRPO loop. Counterfactual Information Gain (CIG) compares the gold-answer log-likelihood under a frozen reference model with and without the user response, providing per-turn credit that guides how to ask. The Asymmetric Ambiguity Bonus assigns a signed reward at the terminal token based on the gold ambiguity label, guiding when to ask. Across three clarification benchmarks spanning table, passage, and open-domain QA, CIGAsk-7B outperforms the strongest external baseline despite using a smaller backbone. It also transfers across datasets without per-dataset tuning while preserving single-turn QA performance on out-of-distribution benchmarks.