The cultural context in the United States is racialized and influences Black Caribbean immigrants' acculturation processes, but what role it plays in Black Caribbean immigrants' acculturation into specific facets of American society (e.g., African American culture) has been understudied in the field of psychology. The present study extends research on Black Caribbean immigrants' acculturative process by assessing how this group's experience of the racial context (racial public regard, ethnic public regard, and cultural race-related stress) influences its engagement in African American culture (i.e., adoption of values and behavioral involvement). Data were collected from 93 Black participants of Caribbean descent, ranging in age from 13 to 45 and analyzed using a stepwise hierarchical regression. The findings highlighted that when Black Caribbean-descended participants perceived that the public held a favorable view of their racial group they were more likely to engage in African American culture. In contrast, when participants perceived that the public held a favorable view of their ethnic group (e.g., Haitian) they were less likely to engage in African American culture. Furthermore, among participants experiencing low levels of cultural race-related stress, the associations between racial public regard and engagement with African American culture were amplified. However, for participants experiencing high cultural race-related stress, their engagement in African American culture did not change as a function of racial public regard. These findings may suggest that, for Black Caribbean immigrants, the experience of the racial context influences strategies that serve to preserve or bolster their overall social status and psychological well-being in the United States.