arXiv:2604.22313v1 Announce Type: new Abstract: NL2SQL systems deployed in industry settings often encounter ambiguous or unanswerable queries, particularly in interactive scenarios with incomplete user clarification. Existing benchmarks typically assume a single source of ambiguity and rely on user interaction for resolution, overlooking realistic failure modes. We introduce Clarity, a framework for automatically generating an NL2SQL benchmark with multi-faceted ambiguities and diverse user behaviors across both single- and multi-turn settings. Using a constraint-driven pipeline, Clarity transforms executable SQL into ambiguous queries, augmented with grounded conversational continuations and schema-level metadata. Empirical evaluation on Spider and BIRD shows that leading NL2SQL systems, including those based on strong LLMs, suffer significant performance degradation under multi-faceted ambiguity. While these systems often detect ambiguity, they struggle to accurately localize and resolve the underlying schema-level sources. Our results highlight the need for more robust ambiguity detection and resolution in industry-grade NL2SQL systems.