Research on ethnic-minority youths' mental health has rarely examined developmental trajectories for the same ethnic group in contexts where they are a minority versus where they are the majority or mechanisms accounting for differences in trajectories across such contexts. This study examines Puerto Rican youth residing in two contexts, one in which they are in their home culture of Puerto Rico and one in which they are a minority group, in New York. We explore the relationship among social context, minority status, risk, resilience, and trajectories of internalizing symptoms after adjusting for factors related to migration. We found that youths' reports of internalizing symptoms declined over time. Youths in New York had higher levels of internalizing symptoms than did youths in Puerto Rico, but they had similar trajectories. Differences in internalizing symptoms across the two social contexts were accounted for by experiences of discrimination and exposure to violence. Parental monitoring was associated with fewer internalizing symptoms across the two sites, although this effect diminished over time. Contrary to what was expected, family religiosity was associated with higher levels of internalizing symptoms. This association was stronger in New York than in the Puerto Rico site.