In the current study, we examine patterns of school attendance across middle and high school with a diverse sample of 8,908 students (48% female; 54% Latino, 31% White, 13% African American, 2% Asian American). Attendance declined from middle through high school, but this overall pattern masked important variations. In total, 44% of students maintained their attendance trajectories from middle to high school (11% stable high, 19% high-decreasing, 10% mid-decreasing, 4% low-decreasing), and shifting attendance trajectories often signaled greater school disengagement (38% shifted to poorer attendance trajectories, 18% experienced improved attendance trajectories). Transition experiences, school structural characteristics, and the divergence between students' middle and high schools provided insights into which students recovered, becoming more engaged in high school versus those who became more disconnected. Implications for identifying and intervening with disengaged youth are discussed.