This study identified maternal and infant characteristics predicting human milk (HM) feeding in very low birth weight (VLBW) infants whose mothers (n = 184) participated in a study of lactation counseling and initiated milk expression. Data were collected prospectively, by maternal interview and medical record review. During hospitalization, 159 (86%) infants received at least 50% HM proportion of feedings in the first 2 weeks of life, and 114 (62%) received some HM until the day of hospital discharge. Analysis showed plan to breastfeed was the strongest predictor of initiation and duration of HM feeding. Greater than 12 years of education, respiratory distress syndrome, Apgar score >6, and female gender were significant predictors, and no perinatal hypertensive disorder, white race, and mechanical ventilation were marginal predictors of HM feeding. Women with a high-risk pregnancy should be provided education about the benefits of breastfeeding for infants who are likely to be born prematurely.