This workshop examines the limitations and usefulness of AI systems that might provide expert-level information to multiple actors in the legal system. Using a simulated medical malpractice case, participants in the workshop will explore three levels of information that an AI model might provide in the case. The first level involves information that an AI system might provide to a potential litigant seeking to better understand both their medical treatment and legal options following a health injury. The second level involves information that an AI system might provide to a lawyer seeking to understand the medical aspects of the case. The third level involves information that an AI system might provide to a judge who decides the case by applying legal rules to complex medical facts. The workshop organizers will prepare questions designed to obtain information at each level.