Health care for the homeless is a major problem in American communities. Understanding the gaps, barriers and limitations in this system is imperative to providing homeless populations appropriate care. This research aims to understand the gaps in the homeless system of Worcester, Massachusetts through interviews with hospital staff and employees of agencies working with the homeless population. Analysis revealed an extremely divided system between provision of health care and provision of social services to Worcester’s homeless population. Across these two systems there was limited to no collaboration, communication and understanding. In order to provide more adequate care to homeless individuals, the author outlines solutions in the areas of education, collaboration, infrastructure, and public policy. Issues experienced by the city of Worcester are similar to those experienced in other American cities and this research can help guide other communities also looking to improve the intersection of health care and homelessness.