Caribbean immigrant students, who represent one of the largest subgroups in the Black population in the United States, are experiencing negative educational outcomes that are related to poor academic achievement and high dropout rates. These academic problems have been partially connected to the negative experiences Caribbean students and their families have within schools, particularly poor interactions with school personnel (Albertini, 2004; Fine et al., 2004). This article discusses the cultural values, historical experiences, and socio-political issues of Caribbean immigrants as a foundation for understanding appropriate school counseling interventions in working with this population. …