The mother of a high risk infant is confronted with numerous parenting challenges, not the least of which is the decision about how to nourish her vulnerable newborn. Successful breastfeeding depends on overcoming obstacles posed by infant condition, maternal health, and the neonatal intensive care environment. These obstacles include maternal separation from the nursing infant during hospitalization, delayed initiation of the expression of breast milk due to maternal illness and/or surgery, the inability to suckle her infant or feed on demand, and the lack of sufficient maternal follow-up after discharge. This article reviews the benefits of providing breast milk to high risk infants, problems that may be encountered by mothers of high risk infants, and the interventions that may be used by the midwife to facilitate the breastfeeding process.