Immigrant students from the English-speaking Caribbean face various forms of psycho-educational and socio-cultural dislocation in their attempt to fit within the structures of their new schools and communities in the United States. These students risk academic failure and delinquency and the possibility of remaining on the periphery of American society, unless schools assume the central role of fostering a smooth transitional process for them. Despite the critical role that teachers, social workers, guidance counselors, and school psychologists play in shaping the transitional outcome of immigrant students, to date, there has been no serious effort to examine the experiences of these service providers who work with the spiraling numbers of school-age Caribbean students. This study utilizes qualitative methods to gain insight into the experiences of teachers and related professional staff from two NYC schools, which serve large numbers of Caribbean students of African and East Indian heritage. In particular, it explores the polices and procedures that schools enact to ensure a smooth transition, and the level of cultural competence that teachers and other professional staff bring to bear in their work with these children. The study is guided by theoretical formulations of empowerment-based practice, including the strengths perspective and NASW standards for cultural competence in social work practice. (Contains 1 table.)