Homelessness in the United States is decreasing. However, homeless persons exhibit high levels of illness and frequently move between institutional and community settings. These moves are complicated by a complex health care and service industry landscape that is often difficult to navigate. In this article, we describe an innovative transitional care program for homeless persons that augments nurse-led transitional care with community health workers who provide accompaniment and linkage to services for program participants. This model offers promise in surmounting the myriad structural barriers to health and health care that many homeless persons in our communities routinely face.