Background: The development of youth psychopathology may be associated with direct and continuous contact with a different culture (acculturation) and to distress related to this process (cultural stress). We examine cultural experiences of Puerto Rican families in relation to youth psychiatric symptoms in two different contexts: one in which migrant Puerto Ricans reside on the mainland as an ethnic minority and another in which they reside in their place of origin. Methods: "Sample": Probability samples of 10- to 13-year-old youth of Puerto Rican background living in the South Bronx, New York City (SB) and in the San Juan Metropolitan area in Puerto Rico (PR) (N = 1,271) were followed over time. "Measures": Three assessments of internalizing psychiatric symptoms (elicited through the DISC-IV) and of antisocial behaviors (ASB) quantified through a six-point index were carried out. Independent variables included scales of adult and child acculturation and cultural stress, and other putative correlates. "Data analysis": Within each study site, multilevel linear regression models were examined. Results: Parental acculturation was associated with ASB in youth at both sites, but youth acculturation itself was not related to psychiatric symptoms. At both contexts, cultural stress was a more consistent correlate of youth psychiatric symptoms than acculturation after controlling for nativity, maternal education, child gender, stressful life events and parental psychopathology. However, the strength of the youth cultural stress association decreased over time. Conclusion: The association between cultural factors and child psychiatric symptoms is not restricted to contexts where an ethnic group is a minority.