InfoQuest: Evaluating Multi-Turn Dialogue Agents for Open-Ended Conversations with Hidden Context

While large language models excel at following explicit instructions, they often struggle with ambiguous or incomplete user requests, defaulting to verbose, generic responses rather than seeking clarification. We introduce InfoQuest, a multi-turn chat benchmark designed to evaluate how dialogue agents handle hidden context in open-ended user requests. The benchmark presents intentionally ambiguous scenarios that require models to engage in information-seeking dialogue through clarifying questions before providing appropriate responses. Our evaluation of both open and closed-source models reveals that while proprietary models generally perform better, all current assistants struggle with effectively gathering critical information, often requiring multiple turns to infer user intent and frequently defaulting to generic responses without proper clarification. We provide a systematic methodology for generating diverse scenarios and evaluating models' information-seeking capabilities, offering insights into the current limitations of language models in handling ambiguous requests through multi-turn interactions.