The present qualitative research focuses on homeless fathers living with their children in family shelters. Data were collected through semistructured, face-to-face interviews with homeless fathers (n = 9) and shelter directors (n = 3). Findings suggest that how fathers made meaning of their experiences in a homeless shelter was related to contextual factors and constructions of masculinity. Contextual constraints deriving from unemployment, behavioral and psychological restrictions of shelters, and new parenting roles led men to reassess their parental and masculine role identities. Results further suggest that homeless shelters may provide a unique point for intervention services to assist poor fathers.