Researchers and practitioners often assume that positive and negative outcomes are inversely correlated. Youth development can be more complex than a simple linear association, however. This complexity is poorly understood, with more research needed to inform how such associations manifest among specific populations and how sociodemographic factors may drive variation in those associations. Framed by the specificity principle and the broader relational developmental systems metatheoretical framework, the two studies in this dissertation explored how associations between positive and negative outcomes manifest in a sample of immigrant youth in the United States. In Study One, I examined the associations between positive outcomes—flourishing and school engagement—and negative outcomes—depression, anxiety, and behavior problems—and considered specificity in those associations by examining the influence of race, sex, immigrant generation, and family poverty level. Without moderation, positive and negative outcomes were inversely correlated. When specificity was accounted for, race, sex, and family poverty level significantly moderated the associations in ways that suggested complexity. In Study Two, I examined if and how discrimination moderated the same associations, and explored further specificity by examining the additional influence of race using three-way interactions. Associations between flourishing and internalizing problems tended to be complex for youth who had experienced discrimination. Associations between school engagement and depression and behavior problems tended to be less complex among those who had experienced discrimination compared to those who had not. Discrimination moderated the associations differently for immigrant youth of different races. Results from this dissertation suggest equifinality in youth pathways to developmental outcomes and highlight the need to incorporate specificity into research, interventions, and programs serving youth.