Homelessness and incarceration share a bidirectional association: individuals experiencing homelessness are more likely to be incarcerated and former inmates are more likely to become homeless. Permanent supportive housing (PSH) programs have demonstrated positive outcomes for participants with criminal histories, yet participants continue to exit to jail or prison and experience subsequent homelessness. Using data on Veterans participating in a PSH program at 4 locations between 2011 and 2014 (N = 1,060), logistic regression was used to examine the risk factors for exiting PSH because of incarceration and returning to homelessness. Though exiting because of incarceration was uncommon, Veterans with a drug use disorder who decreased the frequency of related care over time had an increased risk for this outcome, and a history of incarceration increased Veterans’ risk of experiencing ongoing homelessness. Findings can inform housing and reentry interventions which should account for participant risk factors and service needs in an effort to end the cycle of homelessness and incarceration.