A substantial literature documents a gender reversal in many aspects of social psychological functioning during adolescence, in which girls fall below boys in domains in which they once enjoyed advantages. This study elaborates upon recent research from the National Longitudinal Study of Adolescent Health suggesting that this phenomenon may occur in school attachment, an aspect of educational adjustment. Our analysis of grade 7 through 12 students revealed a gender reversal in school attachment only among whites; although gender differences at each grade level were quite small, the larger differences among girls produced the reversal pattern. Self-esteem, depressive symptoms, and relationships with parents appear to be key factors tied to this reversal but ultimately do not account for grade level differences among girls. We also found that the paradoxical coupling of girls' higher achievement with lower attachment in the upper grades resulted from a weaker association between attachment and achievement among girls than among boys, especially in the upper grades. (Contains 1 figure, 2 tables and 9 footnotes.)