People who become homeless for the first time in late life are a growing but understudied population. This study draws on administrative data from one shelter (N = 1,214 first-time homeless) to assess the extent to which age is related to shelter stay and, to examine psychosocial factors that may be associated with shelter departure. Our bivariate and survival analysis results suggest that older homeless men stay in the shelter 2 weeks longer than younger clients. Older men with pending legal issues and mobility concerns were more likely to leave the shelter than those without such concerns. Findings highlight the impact of age and other psychosocial variables on shelter stay, and provide direction from which to address homelessness among men who are new to homelessness in later life.