Relations between classroom behavior problems early in the preschool year and elementary school literacy and language outcomes were examined for an entire cohort of four-year-old Head Start children (N=2682). A cross-classified random effects model was used that controlled for the variance in literacy outcomes attributed to: (a) child-level demographics (age, gender, ethnicity), and end of the preschool year cognitive skills; (b) Head Start, kindergarten and first grade classrooms; and (c) kindergarten and first grade schools. Preschool behavior problems were assessed across structured learning situations, and during peer and teacher interactions at the beginning of Head Start. Preschool behavior problems in structured learning situations differentially predicted lower literacy outcomes across all time points. Findings extend previous research and underscore the importance of early identification of problem behavior using developmentally and ecologically valid tools within early childhood classrooms intentionally designed to foster literacy skills. (Contains 7 tables.)