The current study tests a prediction of Relational Discrepancy Theory (RDT; i.e., emotional distress will not accompany discrepancies in hierarchical relationships) for family obligations discrepancies among adolescent–parent dyads in Jamaica, a moderately collectivistic and hierarchical society. Ninety-five dyads reported psychological adjustment and discrepancies in family prioritization (i.e., value priority placed on family vs. other life domains). Results supported RDT and replicated recent work with Caribbean immigrants in Europe. Unlike findings in individualistic and egalitarian societies, discrepancies were not an emotional liability for Jamaican adolescents but were associated with fewer depressive symptoms and higher life satisfaction. Furthermore, Jamaican parents benefitted psychologically when adolescents prioritized family highly but may have been unaware of the emotional risks to their teenagers of matching parental expectations.