This study examined how the developmental processes of autonomy and relatedness are related to changes in the residential status of 181 first-time, adolescent, urban, low-income, African American mothers over the first 24 months postpartum. Although adolescent mothers were eager to live independently, few made a clear transition out of the multigenerational household; 56% lived in the household of origin continuously (IN), 21% left and never returned (OUT), and 23% had multiple moves in and out of the household (IN/OUT). Older adolescent maternal age, less supportive adolescent mother-grandmother relations, and high household density were associated with leaving the household of origin. The IN/OUT group had difficulty adopting the roles of adult and parent. Helping adolescent mothers and grandmothers negotiate roles to reduce conflict may promote autonomy and relatedness, allowing mothers to learn parenting skills, qualify for public assistance, and continue their education.