We examined different dimensions of acculturative stress in mediating the association between acculturation and psychosocial functioning among 199 Cuban American college students (M age = 20.1 years) in Miami. Results showed that heritage-cultural orientation was directly associated with self-esteem. No other direct relations emerged. Spanish competency pressures and pressures against acculturation mediated the relationships between heritage-cultural orientation and internalizing symptoms, whereas pressures to acculturate mediated the association between American cultural orientation and self-esteem. These findings highlight the unique roles of different components of acculturative stress in the relationship of heritage and American cultural orientation to Cuban American adolescents' psychosocial well-being. Implications regarding the multidimensionality of acculturation and of acculturative stress are discussed.