Research on child and family factors in early childhood has shown that both are associated with social and instrumental functioning at school entry. The present study sought to examine the direct and indirect effects of child negative emotionality, maternal education, depression, IQ, and quality of maternal instruction on children's academic and emotion regulatory behaviors from the toddler period to school entry using a sample of 174 boys from low-SES backgrounds. Results revealed direct effects of maternal IQ on academic outcomes at school entry that were mediated by maternal instruction. Further, maternal instruction predicted the child's academic and emotion regulation (ER) outcomes even after accounting for other maternal and child variables. The effects of both instruction variables moderated the impact of maternal education. The results suggest that maternal instruction plays an important role in early school success, particularly for children at risk for school problems.