This study expands research on an academic and social turning point for adolescents, the transition to high school, by analyzing how students' level of social integration into school can affect high school academic performance. Using nationally representative data, three different pathways emerged as students transition to high school, characterized by varying amounts of disruption and opportunity for new social relationships upon entering high school. Findings suggest that elements of middle school social integration, including teacher bonding, popularity, and extracurricular participation, affect academic achievement when students enter high school. However, the association between integration into school and academic performance appears to be contingent upon the pathway students follow.