In the American K-12 educational system, school transitions are frequent and predictable--typically occurring when students enter kindergarten and when they move from elementary to middle school and again from middle to high school. Although much is known about the short- and long-term implications for the transition to formal K-12 schooling and the transition into middle school, how the transition to high school influences the immediate and long-term educational prospects of American students is relatively unknown and is the focus of the current study. Specifically, the author sought to determine whether the high school transition influences students' educational engagement (as assessed by attendance), which students are most at risk for experiencing transition difficulties as they move from 8th to 9th grade, in what types of schools are students doing best, and how success or challenges across the high school transition affects students' educational trajectories across high school and their early educational attainment. The findings suggest that it is not just 9th grade attendance, but it is the disruptions in attendance that students face as they negotiate physically moving from middle school to high school that can derail educational trajectories. Addressing Texas's ninth grade problem is important for ensuring the state increases its number of highly qualified high school graduates and that these high school graduates make successful transitions to college and the world of work, and the current study suggests that Texas schools and districts should place strong attention on enacting intervention strategies that better support students as they move from middle to high school.