Most of the research literature on attachment and adolescent transitions has addressed youth in family settings. This article explores these issues with a sample of 25 pregnant and parenting teens living in a transitional shelter. Using case records and interview data as well as results of standardized measures of depression, self-esteem, child abuse potential, and emotional autonomy, insights on relationships between adolescent mothers and their parents, romantic partners, staff, and children are explored, and implications are provided for agencies serving this population.