Background: Breastfeeding is the biological norm and is associated with numerous superior health outcomes for children and mothers when compared to human milk substitutes. Yet, breastfeeding difficulties and the inability to meet one’s breastfeeding goals are common in the United States and maybe more common among mothers who have experienced trauma. Research Questions: (1) Are mothers’ adverse childhood experiences, and current experiences of discrimination, material hardship, and decreased social support associated with breastfeeding challenges; and (2) are these experiences associated with the number of breastfeeding challenges reported? Methods: A prospective, non-probability, cross-sectional study design with a diverse sample who had delivered a live baby within the previous year ( N = 306) was conducted. Results: Over 70% of participants reported breastfeeding challenges and 45.2% reported material hardship. Among those who attempted breastfeeding ( n = 286), 74.1% had at least one adverse childhood experience; 30.3% had four or more. Logistic and negative binomial regression models determined that adverse childhood experiences, experiences of discrimination, material hardship, and decreased social support were not associated with experiencing any breastfeeding challenges. However, adverse childhood experiences were associated with the number of breastfeeding challenges reported. (The adjusted rate ratio was 1.05; 95% CI [1.00, 1.09], p = .034). Conclusion: We recommend further research on adverse childhood experiences and potential relationships with discrimination, material hardship, and social support to prevent and intervene in cases of breastfeeding challenges to maximize infant, maternal, and public health.