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Objective: Although breastfeeding provides benefits for mothers and infants, multiple factors prevent women from breastfeeding. This article aims to explore the role of mothers' personal and contextual risk factors to breastfeeding rates with a special emphasis on understanding breastfeeding among African American mothers at 6 months postpartum. Design: This secondary analysis was capitalizing on previously collected postpartum data from a longitudinal cohort study on the consequences of maternal childhood trauma on mother and infant outcomes. Postpartum mothers (n = 188) completed questionnaires on demographics, childhood trauma history, postpartum depression, social support, and breastfeeding status at 6 months postpartum. Results: All risk factors (i.e., demographic and social support risk, childhood trauma history, and postpartum depression) were associated with lower breastfeeding at 6 months postpartum. When risk factors were examined in a single comprehensive model, only cumulative demographic risk emerged as significant. When partialing-out by race, being African American was the only variable associated with lower breastfeeding at 6 months postpartum. Conclusions: Our study confirms that African American mothers report lower breastfeeding rates at 6 months postpartum than non-African American mothers. This association held even when controlling for demographic and social support risk, childhood trauma history, and postpartum depression. We discuss our findings from an intergenerational and historical trauma, racism, chronic discrimination perspective that considers the multifactorial nature of past and current impacts on breastfeeding among African American women in the United States.