AI-Assisted Moot Courts: Simulating Justice-Specific Questioning in Oral Arguments

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.

Legal Retrieval for Public Defenders

AI tools are increasingly 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 legal retrieval benchmarks fail to transfer to public defense search, 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 provide a taxonomy of realistic defender search queries and release a manually annotated public defense retrieval dataset. Together, our work offers starting points towards building practical, reliable retrieval AI tools for public defense, and towards more realistic legal retrieval benchmarks.