This article presents information from interviews and questionnaires administered to 4,582 kindergartners who were former Head Start participants and their primary caregivers. Also, students' kindergarten, first-, and second-grade teachers rated their academic performance. Most children (74%) had extremely positive perceptions of all aspects of school. However, a subset of children (7%) reported they did not like school very much and were not doing well; further, they reported that they and their parents did not highly value doing well in school. These children with less positive school perceptions were significantly more likely to be boys and to have lower receptive language skills (as measured by the Peabody Picture Vocabulary Test) than children with more positive perceptions. Rates of special education placement and family risk variables (i.e., single-parent status, income, welfare status, mother's age, parent education, parent working status) did not differ for children with higher and lower ratings of school. Parents had highly favorable impressions of children's early school adjustment, even more favorable than their children's. Teachers' ratings of children's academic performance were significantly higher for children with more rather than less positive school perceptions in kindergarten, first, and second grades. Efforts needed to minimize poor transition-to-school experiences and to identify children with negative perceptions of school as early as possible are discussed.