Abstract: Breastfeeding is beneficial for the baby and the mother, but is yet to be successfully practiced by newly delivered women as proposed in the Healthy People 2020 goal. Most breastfeeding education during the prenatal or postpartum period provides adequate information for interested women. However, mothers need individualized client–professional interactions and follow-up after hospital discharge. This article describes the breastfeeding experiences of two women and the implications for nurses and other healthcare professionals in relation to efforts to promote breastfeeding. Two anecdotal case studies are presented illustrating that even when mothers have resources and education, the breastfeeding education can be frustrating and misunderstood. Nurses can master the skill of closing the feedback loop in breastfeeding education by assessing and clarifying women's interpretation of breastfeeding information they received. This nursing skill can empower mothers to make informed decisions for effective and sustained breastfeeding.