Research Findings: The purpose of this study was to examine whether child temperament differentially predicted academic school readiness depending on the quality of classroom interactions for 179 Head Start preschoolers. Teachers rated children's temperament as overcontrolled, resilient, or undercontrolled in the fall and reported on children's language/literacy and math skills continuously throughout the year. Observations of classroom emotional and instructional support were conducted in the spring. Results from multilevel models indicated that overcontrolled children (compared to resilient children) made greater math gains in classrooms with higher instructional support, whereas a trend-level effect suggested that undercontrolled children (compared to resilient children) made lower math gains in classrooms with lower emotional support. Results also showed that resilient children's gains in language/literacy were more positively associated with high emotional support than were the scores of overcontrolled children. Practice or Policy: This study adds to prior findings suggesting that overcontrolled and undercontrolled children need special attention in the preschool classroom. Teachers and administrators may want to carefully consider the effect that classroom interactions and instructional techniques have on individual children and attempt to tailor instruction to meet the individual needs of children within classrooms. (Contains 4 figures and 3 tables.)