This prospective study examined how characteristics of infants (i.e., birth weight and perinatal illness severity), mothers (i.e., anxiety and level of education), and the social context (i.e., maternal received and perceived helpfulness of support) related to mother-very low birth weight (VLBW) infant interaction in 72 dyads. Infant, mother, and contextual factors were assessed at 3 and 9 months of age, and mothers and infants were observed in teaching interactions at 9 months. Dyads whose interaction was more sensitive and responsive included mothers who were better educated and less anxious at 3 months and reported higher perceived support at 3 months. The findings highlight the importance of maternal education and well-being in the parenting of VLBW infants.