Local jails in the United States incarcerate millions of people each year. The COVID-19 pandemic made jail health a pressing public health concern nationally, where releasing individuals from jails occurred across the country in order to prevent pandemic spread. But releases also faced substantial resistance and exposed long-standing challenges in delivering adequate healthcare in jail settings. People in jail have substantially higher levels of medical need than individuals in the general population, with large numbers having serious mental illnesses and substance use disorders. Further, overcrowded conditions and poor healthcare standards and delivery make jails harmful to those already-vulnerable people. What means exist to protect individuals whose health would suffer in jail? Constitutional standards under the Eighth Amendment are highly deferential to jail administrators, nor is there substantial state or local level regulation of jail health. However, more informal mechanisms do exist, and they may be more responsive to health-based needs than constitutional or legal rights. 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. The Article describes widespread informal and unwritten mechanisms for health-based releases from jails. The Article will present the data and how such practices have implications for reforming the legal rules surrounding jail healthcare.