Although children born preterm or low birth weight (PT LBW) are more likely to exhibit behavior problems compared to children born at term, developmental and family processes associated with these problems are unclear. We examined trajectories of maternal depressive symptoms in relation to toddler compliance and behavior problems in families with PT LBW infants. A total of 177 infants (93 boys, 84 girls) and their mothers enrolled in the study during the infant's NICU stay. Data were collected at five time points across 2 years. Assessments of maternal depressive symptoms were conducted at all time points, and toddler compliance and opposition to maternal requests and behavior problems were assessed at 2 years. Toddlers born earlier with more health problems to mothers whose depressive symptoms increased over time exhibited the most opposition to maternal requests during a cleanup task at 24 months, consistent with multiple risk models. Mothers with elevated depression symptoms reported more behavior problems in their toddlers. The study has implications for family-based early intervention programs seeking to identify PT LBW infants at highest risk for problem behaviors.