While most mothers initiate breastfeeding, many do not continue for recommended durations. This study aimed to understand the gap between breastfeeding initiation and duration through an in-depth exploration of first-time mothers’ breastfeeding experiences. Contextual factors that may facilitate or deter breastfeeding maintenance were explored by identifying common turning points (significant events or periods promoting a change in thoughts/behaviors or facilitating maintenance) described by mothers with varied breastfeeding durations. In semistructured interviews conducted from March to June 2015, twenty-eight first-time mothers in Iowa were asked to describe their breastfeeding experiences from initiation through cessation. Using thematic analysis, seven turning points, consistent across varied durations and experiences were identified: breastfeeding problems, the unknowns, recurring stressors, living new life with baby, reentering social roles, special occasions, and letting go. Turning points were usually associated with stressful situations, and mothers described intrapersonal (e.g., determination) and interpersonal (e.g., social support) coping resources as facilitators of breastfeeding maintenance. These findings highlight contextual factors that may trigger turning points, representing critical intervention periods, and the importance of enhancing support networks. Interventions to facilitate longer breastfeeding durations should consider key turning points and availability of coping resources to determine strategies that best fit the mother at each point.