We characterized breastfeeding concerns from open-text maternal responses and determined their association with stopping breastfeeding by 60 days (stopping breastfeeding) and feeding any formula between 30 and 60 days (formula use). We assessed breastfeeding support, intentions, and concerns in 532 expectant primiparas and conducted follow-up interviews at 0, 3, 7, 14, 30, and 60 days postpartum. We calculated adjusted relative risk (ARR) and adjusted population attributable risk (PAR) for feeding outcomes by concern category and day, adjusted for feeding intentions and education. In 2946 interviews, 4179 breastfeeding concerns were reported, comprising 49 subcategories and 9 main categories. Ninety-two percent of participants reported ≥ 1 concern at day 3, with the most predominant being difficulty with infant feeding at breast (52%), breastfeeding pain (44%), and milk quantity (40%). Concerns at any postpartum interview were significantly associated with increased risk of stopping breastfeeding and formula use, with peak ARR at day 3 (eg, stopping breastfeeding ARR [95% confidence interval] = 9.2 [3.0-infinity]). The concerns yielding the largest adjusted PAR for stopping breastfeeding were day 7 "infant feeding difficulty" (adjusted PAR = 32%) and day 14 "milk quantity" (adjusted PAR = 23%). Breastfeeding concerns are highly prevalent and associated with stopping breastfeeding. Priority should be given to developing strategies for lowering the overall occurrence of breastfeeding concerns and resolving, in particular, infant feeding and milk quantity concerns occurring within the first 14 days postpartum.