In recent years, permanent supportive housing (PSH) has emerged as the preferred intervention for addressing chronic homelessness in the United States. However, almost all prior studies examining the effectiveness of PSH have been conducted at the individual level, with only minimal attempts to empirically test the relationship between PSH and chronic homelessness at the community level. This study uses longitudinal data collected by the US Department of Housing and Urban Development (HUD) and several other sources to model the relationship between measures of community investment in PSH and rates of chronic homelessness. The results show modest negative associations between increased investment in PSH and rates of chronic homelessness over time. We discuss the implications of these findings for ongoing efforts to address chronic homelessness and future research. © 2014 by The University of Chicago. All rights reserved.