The level of out-migration from the Caribbean is very high, with migration of tertiary-level educated populations from Caribbean countries being the highest in the world. Many clinicians in receiving countries have had limited diagnostic and therapeutic experience with Caribbean migrants, resulting in diagnostic and therapeutic controversies. There is an urgent need for better understanding of these cultural differences. The paper explores issues of clinical and cultural competence relevant to assessing, diagnosing, and treating Caribbean migrants with a focus on three areas: cultural influences on illness phenomenology; the role of language differences in clinical misunderstandings; and the complexities of culture and migration. Clinical issues are illustrated with case studies culled from four decades of clinical experience of the first author, an African Jamaican psychiatrist who has worked in the Caribbean, North America, Europe, and New Zealand.