This report from The Pew Charitable Trusts explores how jails administer their health care programs and whether these programs further county public health and safety goals. Research is limited on how counties organize their jail health care services, what care they make available and when, and how they ensure they receive value for their investment in health care. Despite growing awareness of the connection between community services for recently released individuals—especially those with mental illness or substance use disorders—and a reduction in recidivism, information about how to achieve this result is scarce. As such, with the assistance of Community Oriented Correctional Health Services, The Pew Charitable Trusts reviewed 81 requests for proposals for contracted jail health care services and conducted in-depth case studies of three jurisdictions. The research revealed wide variation in the ways that counties arrange to provide health care in their jails and the information they supply to help vendors craft bids.