Caribbean immigrants' challenges with acculturation following immigration to the United States, could result in acculturative stress, discrimination, stereotyping, and mental health issues. This study examined the relationship between cultural levels of interaction (LCI), acculturation orientation levels (AOLs), and acculturation levels (ALs) as well as examined the relationship between acculturative stress levels (ASLs), mental health problems, and discrimination/ stereotyping among Caribbean immigrants, age 25-54, in a northeast U.S. metro. Bourhis' interactive acculturation model was the theoretical foundation for this study. It was hypothesized that (a) there would be a relationship between LCI measured in language, food, religion, and education and AOL or AL and (b) there would be a relationship between ASL and mental health problems (negative coping, depression, anxiety, and general life stress) or discrimination/ stereotyping. This research used a survey design, with 138 participants; analyses included Pearson correlations and multivariate multiple linear regression. Results revealed that the LCI group was significantly associated with Caribbean immigrants' AOLs, but food was not significant to their ALs. Additionally, ASL was significantly related to discrimination/ stereotyping, depression, anxiety, general life stress, and negative coping. This research may facilitate social change by urging clinicians to more effectively address preventive care for mental health problems in Caribbean immigrants. Educating society about the economic and other contributions of this population could also decrease discrimination/ stereotyping. Further, the study's findings may lead to initiatives for transitioning new arriving Caribbean immigrants.