Nimra Nadeem

Dominik Stammbach, Kylie Zhang, Patty Liu et al.

AI tools are suggested as solutions to assist public agencies with heavy workloads. In public defense -- where a constitutional right to counsel meets the complexities of law, overwhelming caseloads, and constrained resources -- practitioners face especially taxing conditions. Yet, there is little evidence of how AI could meaningfully support defenders' day-to-day work. In partnership with the New Jersey Office of the Public Defender, we develop the NJ BriefBank, a retrieval tool which surfaces relevant appellate briefs to streamline legal research and writing. We show that existing retrieval benchmarks fail to transfer to real public defense research, however adding domain knowledge improves retrieval quality. This includes query expansion with legal reasoning, domain-specific data and curated synthetic examples. To facilitate further research, we release a taxonomy of realistic defender search queries and a manually annotated evaluation dataset for public defense retrieval. This benchmark is highly correlated with a proprietary retrieval dataset annotated by experienced public defenders. Our work improves on the status quo of realistic legal retrieval benchmarking and illustrates one approach to applying AI in a real-world public interest setting.

Luxi He, Nimra Nadeem, Michel Liao et al. · princeton

AI systems are increasingly governed by natural language principles, yet a key challenge arising from reliance on language remains underexplored: interpretive ambiguity. As in legal systems, ambiguity arises both from how these principles are written and how they are applied. But while legal systems use institutional safeguards to manage such ambiguity, such as transparent appellate review policing interpretive constraints, AI alignment pipelines offer no comparable protections. Different interpretations of the same rule can lead to inconsistent or unstable model behavior. Drawing on legal theory, we identify key gaps in current alignment pipelines by examining how legal systems constrain ambiguity at both the rule creation and rule application steps. We then propose a computational framework that mirrors two legal mechanisms: (1) a rule refinement pipeline that minimizes interpretive disagreement by revising ambiguous rules (analogous to agency rulemaking or iterative legislative action), and (2) prompt-based interpretive constraints that reduce inconsistency in rule application (analogous to legal canons that guide judicial discretion). We evaluate our framework on a 5,000-scenario subset of the WildChat dataset and show that both interventions significantly improve judgment consistency across a panel of reasonable interpreters. Our approach offers a first step toward systematically managing interpretive ambiguity, an essential step for building more robust, law-following AI systems.

Kylie Zhang, Nimra Nadeem, Lucia Zheng et al.

In oral arguments, judges probe attorneys with questions about the factual record, legal claims, and the strength of their arguments. To prepare for this questioning, both law schools and practicing attorneys rely on moot courts: practice simulations of appellate hearings. Leveraging a dataset of U.S. Supreme Court oral argument transcripts, we examine whether AI models can effectively simulate justice-specific questioning for moot court-style training. Evaluating oral argument simulation is challenging because there is no single correct question for any given turn. Instead, effective questioning should reflect a combination of desirable qualities, such as anticipating substantive legal issues, detecting logical weaknesses, and maintaining an appropriately adversarial tone. We introduce a two-layer evaluation framework that assesses both the realism and pedagogical usefulness of simulated questions using complementary proxy metrics. We construct and evaluate both prompt-based and agentic oral argument simulators. We find that simulated questions are often perceived as realistic by human annotators and achieve high recall of ground truth substantive legal issues. However, models still face substantial shortcomings, including low diversity in question types and sycophancy. Importantly, these shortcomings would remain undetected under naive evaluation approaches.