Researchers have consistently established the centrality of the reentry experience in understanding offender life course trajectories, and housing has been cited as one of the most central bricks in establishing stable, successful lives. However, the social and structural mechanisms that explain the relationship between housing and parolee outcomes are less known. To explore this, we use in-depth interviews and a grounded theory approach to compare the reentry needs among a sample of male parolees participating in a housing program, Solid Start, with a similar sample of males on traditional parole. The results highlight the centrality of housing and social support during the reentry process, and find that housing services have important implications for structural changes, such as social relationships, and subjective, emotional outcomes. This research adds to the burgeoning literature on reentry transitions by providing narrative accounts of parolee experiences and has important implications for housing assistance programs.