This case study presents a maternal-infant dyad, both of whom bring risk factors to the breastfeeding relationship. The mother had true glandular hypoplasia that was not detected in the antenatal period or during her hospital stay. In addition, the infant was a late preterm infant, bringing the risks of poor feeding behavior and ineffective removal of milk from the breast as well as limited body reserves. Through the use of breastfeeding technology, including test weights, use of a hospital grade double electric breast pump and use of a nipple shield, in addition to a pharmacologic intervention, in which Domperidone was administered, this mother was able to maximize her milk yield and the infant was able to receive human milk for 6 months. This case report highlights the need for a thorough assessment of the breasts as well as the breastfeeding process in all breastfeeding dyads.