Immigration to the United States presents both challenges and opportunities that affect students' academic achievement. Using a 5-year longitudinal, mixed-methods approach, we identified varying academic trajectories of newcomer immigrant students from Central America, China, the Dominican Republic, Haiti, and Mexico. Latent class growth curve analysis revealed that although some newcomer students performed at high or improving levels over time, others showed diminishing performance. Multinomial logistic regressions identified significant group differences in academic trajectories, particularly between the high-achieving youth and the other groups. In keeping with ecological-developmental and stage-environment fit theories, School Characteristics (school segregation rate, school poverty rate, and student perceptions of school violence), Family Characteristics (maternal education, parental employment, and household structure), and Individual Characteristics (academic English proficiency, academic engagement, psychological symptoms, gender, and 2 age-related risk factors, number of school transitions and being overaged for grade placement) were associated with different trajectories of academic performance. A series of case studies triangulate many of the quantitative findings as well as illuminate patterns that were not detected in the quantitative data. Thus, the mixed-methods approach sheds light on the cumulative developmental challenges that immigrant students face as they adjust to their new educational settings. (Contains 2 tables and 1 figure.)