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WinSyn: An Automated Pipeline for Realistic Enterprise Question-Answering Evaluation

arXiv · AI, language, vision and robotics · article · Sep 10, 2026 · UTC

Enterprise settings provide a challenging environment for question-answering agents, which often rely on Retrieval-Augmented Generation, Deep Research (DR), and related techniques. Much of this challenge comes from the complexity of enterprise data: information is often spread across evolving and potentially conflict- ing emails, chat messages, documents, and other artifacts. Existing benchmarks typically have limited real-world complexity, short-form responses, and unnatural queries, so they often fail to capture the challenges of enterprise settings. In this work, we introduce an automated p

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