arXiv:2508.03718v1 Announce Type: cross Abstract: U.S. health insurance is complex, and inadequate understanding and limited access to justice have dire implications for the most vulnerable. Advances in natural language processing present an opportunity to support efficient, case-specific understanding, and to improve access to justice and healthcare. Yet existing corpora lack context necessary for assessing even simple cases. We collect and release a corpus of reputable legal and medical text related to U.S. health insurance. We also introduce an outcome prediction task for health insurance appeals designed to support regulatory and patient self-help applications, and release a labeled benchmark for our task, and models trained on it.