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Evidence from two studies conducted with kindergarten samples (N = 200, M age = 5.58 years; N = 199, M age = 5.47 years) supported a series of interrelated hypotheses derived from a child × environment model of early school adjustment. The findings obtained were consistent with the following inferences: (1) Entry factors, such as children's cognitive maturity and family backgrounds, directly as well as indirectly influence children's behavior, participation, and achievement in kindergarten; (2) as children enter school, their initial behavioral orientations influence the types of relationships they form with peers and teachers; (3) stressful aspects of children's peer and teacher relationships in the school environment adversely impact classroom participation and achievement; and (4) classroom participation is an important prerequisite for achievement during kindergarten. Collectively, these findings illustrate the need to revise prevailing theories of school adjustment, and the research agendas that evolve from these perspectives, so as to incorporate interpersonal risk factors that operate within the school environment.