Children's prior attitudes toward school may be an important entry factor to consider in their initial adjustment to kindergarten. This short-term longitudinal study examined children's affective orientations and other school-related perceptions and approaches to learning in late preschool and then 1 to 2 months after entry into kindergarten. Child, parent, and teacher reports were obtained, and classroom practices were observed. Findings showed that children who anticipated liking school demonstrated more positive approaches and adjustment in kindergarten than did less enthusiastic children. Children's approaches to learning in the classroom, reported by teachers and parents, were similar across the transition from preschool to kindergarten, despite notable differences in practices. Recommendations for practice include attending to children's affective orientations, involving multiple informants in school readiness assessments, and fostering communication among teachers in school transition activities.