Permanent supportive housing (PSH) has been recognized by the U.S. federal government as the "clear solution" to chronic homelessness. Whether and how access to PSH affects HIV risk is unclear. This mixed methods pilot study uses a convergent parallel design in order to better understand social relationships and HIV risk during the transition from homelessness to PSH. Findings suggest that (a) Sexual activity and HIV risk behaviors increase with housing, (b) Social network size and composition appear to change as individuals transition into PSH, and (c) There is tension between moving forward and leaving behind the past once a person has housing. This study demonstrates that PSH constitutes a specific risk environment that has not been previously investigated.