Early identification of risk can support interventions to prevent academic failure. This study investigated patterns of evolution in achievement trajectories for 1,522 high school students in relation to initial achievement, student motivation, and key demographic characteristics. Growth mixture modeling identified 2 classes of longitudinal achievement patterns representing different trajectories toward leaving school either with or without qualifications. Negative motivation patterns on the factors Doing My Best and Doing Just Enough combined with initial student achievement were predictive of underachievement across the final 3 years of senior secondary school. These findings provide empirical support for the use of a simple motivation measure that can enhance identification of risk for school failure and inform interventions for different risk patterns. Boys who were not from the majority culture and who attended large schools in middle socioeconomic status communities were more likely to be on a trajectory for school failure than were girls, majority culture students, and boys in either low- or high-income school communities. Future research is needed to investigate the possibility of increased student risk in large, middle-income schools that may lack the kinds of resources and student supports available in high- and low-income schools.