This dissertation consists of two studies that examined the predictors and consequences of Multiracial youths’ racial-ethnic identification during the middle-to-high school transition. Both studies rely on data drawn from a large, longitudinal study that examined the psychosocial and academic benefits of attending ethnically diverse schools in adolescence. Study 1 examined how objective and subjective changes in the school racial-ethnic context from middle to high school were related to whether Multiracial youth maintained a Multiracial identification or changed to a monoracial identification across the transition to high school. Results indicated that while objective and subjective changes in the racial-ethnic context did not predict Multiracial youths’ identification, the racial-ethnic context in 9th grade did predict Multiracial youths’ identification. More specifically, Multiracial youth were more likely to maintain a Multiracial identification when they attended ethnically diverse high schools and were more likely to change to a monoracial identification when they perceived a greater proportion of same-ethnic peers. Furthermore, differences emerged among Multiracial subgroups such that Latinx-White, Asian-White, and (to some extent) Black-White youth who experienced an increase in same-ethnic representation were more likely to switch to a monoracial identification than Black-Latinx youth. Study 2 assessed how identifying as Multiracial or monoracial upon the transition to high school was associated with ethnic identity and psychosocial adjustment outcomes. To further unpack the role that the school racial-ethnic context may play in shaping these associations, I also tested the moderating role of racial-ethnic diversity of adolescents’ high school contexts. Results revealed that Multiracial youth who switched to a monoracial identification in 9th grade reported feeling less lonely and more ethnic identity exploration than Multiracial youth who maintained a Multiracial identification. Additionally, school racial-ethnic diversity moderated the association for ethnic exploration, such that this effect was stronger in schools that were less racially diverse. Taken together, these studies highlight the importance of taking a critical, context-dependent approach to deepening our understanding of Multiracial youths’ racial-ethnic identification fluidity in order to advance our knowledge of the role that school racial-ethnic context plays in shaping racial-ethnic identification processes and the psychosocial adjustment of Multiracial youth.