This study addressed the needs of low-income, urban children evidencing emotional and behavioral problems within the preschool classroom. Informed by a developmental-ecological model, the study explored the dynamic transactions between behavioral adjustment and the demands of routine, classroom situations. It examined: (a) the latent structure of preschool classroom situations associated with behavioral problems, and (b) the relationships between early problems in these classroom situations and relevant social and learning outcomes. This investigation employed the Adjustment Scales for Preschool Intervention (ASPI), a measure designed to identify behavioral difficulties across multiple preschool situations. It extended prior research (establishing ASPI phenotypic dimensions), by examining the latent structure of the ASPI's 22 routine, classroom situations to determine situational dimensions associated with problematic behavior. Utilizing an archival data set consisting of an entire cohort of Head Start children (N = 3779), exploratory common factor analysis revealed three unique and reliable situational dimensions associated with problems in: Structured Learning, Peer Interaction, and Teacher Interaction. Group differences analyses revealed that boys and younger children evidenced more problematic behavior across all three situations. A second archival data set containing peer social and classroom learning outcomes for a representative cohort of Head Start children (N = 829) was used to establish: (a) convergent and divergent validity for ASPI situational dimensions, (b) the unique contribution of situational dimensions to social and learning outcomes, and (c) the combined contribution of both phenotypic and situational dimensions to social and learning outcomes. Results from hierarchical setwise multiple regression models revealed that early difficulties in situational adjustment uniquely predicted lower peer social and classroom learning competencies at the end of the year. Situational dimensions in combination with previously established phenotypic dimensions, contributed greater total variance than either set alone in predicting preschool outcomes. Results provide evidence for the contribution of distinctive situational dimensions that capture behavioral problems as they arise in transaction between child capacities and classroom demands. The findings are an important step toward creating alternative measurement tools that are appropriate for low-income, preschool children. Implications for early childhood research, practice, and policy are discussed. (author abstract)