This paper “shares insights from the experiences of five jurisdictions working to implement different forms of HIT connectivity. Although there is no turnkey solution, there are lessons to be learned. [The] intent here is to share these lessons with those interested in improving health care in jail environments and with jurisdictions that are looking for ways to create connectivity in their communities” (p. 5). Sections of this report cover: bridging the islands between jail management systems, jail health systems, and community health systems; three guiding principles for connectivity-policy, resources, and champions; and HIT (health information technology) connectivity in Orlando County (FL), Multnomah County (OR), New York City, Hampden County (MA), and Fayette County (KY).