This article describes insights from qualitative interviews with jail medical staff in four states, to explore what challenges face delivery of healthcare, but more specifically, when health-based needs require counsel releasing individuals from jail. It describes widespread informal and unwritten mechanisms for health-based releases from jails and how such practices have implications for reforming the legal rules surrounding jail healthcare. By: Brandon L. Garrett, Deniz Ariturk, Jessica Carda-Auten, and David L. Rosen — William and Mary Bill of Rights Journal (2022).