This study examined growth patterns in adaptation of immigrant youth from a risk and resilience perspective. Students from first- and second-generation immigrant families living in Greece and their nonimmigrant classmates (N = 1,057) were assessed over the first 3 years of secondary school (ages 13–15). Three-level hierarchical linear models were used to disentangle individual and classroom-level effects on initial level and change in academic achievement, conduct, peer popularity, and psychological well-being. At the individual level, adaptation was more related to self-efficacy and parental school involvement (resources) than immigrant status and social adversity (risks). Only for academic achievement did risks explain variance when resources were controlled. Parental school involvement moderated the effect of immigrant status for initial level and growth in achievement. For all students, achievement and conduct worsened over time. At the classroom level, socioeconomic and ethnic composition of the classroom moderated the effects of self-efficacy and immigrant status on academic achievement and peer popularity, respectively. Second-generation immigrants were more popular than first-generation immigrants, but showed a larger decrease over time in school achievement. Results support a developmental, differentiated, and contextualized approach to the study of immigrant youth adaptation.