The 1976 Supreme Court decision in Estelle v. Gamble declared that jails must provide medical treatment to detainees consistent with community standards of care. Yet despite their important role providing health care to about ten million people a year, jails remain largely siloed from the surrounding health care community, compromising inmates’ health and adding to health care spending. Health information technology promises solutions. The current policy landscape, shaped by the Health Information Technology for Economic and Clinical Health (HITECH) Act and the Affordable Care Act, is favorable to jails’ implementation of health information technology (IT). In this article we examine how decisions largely external to jails—coming from the Supreme Court, Congress, and local policy makers—have contributed to the growth of health IT within jails and health information exchange between jails and local communities. We also discuss privacy concerns under the Health Insurance Portability and Affordability Act and other legislation. This article highlights a rare confluence of events that could improve the health of an overlooked population.