Premature newborns and infants are usually required to successfully transition from gavage to nipple feeding using breast or bottle before discharge from the hospital. This transition is frequently the last discharge skill attained. Delayed acquisition of this skill may substantially prolong hospital length of stay. The authors describe a case of hospitalized premature twins who had considerable delays in attaining nipple-feeding skills. Because of their inability to take all feedings by nipple, preparation for surgical placement of gastrostomy tubes was initiated. Before the surgeries were scheduled, the inpatient osteopathic manipulative medicine service was consulted, and the twins received a series of evaluations and osteopathic manipulative treatment (OMT) sessions. During the OMT course, the twins’ nipple feeding skills progressed to full oral feeding, which allowed them to be discharged to home without placement of gastrostomy tubes. The authors also review the literature and discuss the development of nipple feeding in premature newborns and infants and the use of OMT in the management of nipple feeding dysfunction.