The most certain outcome of continued immigration into the United States in the twenty-ﬁrst century is the fact that ethnolinguistic diversity will become the norm. By every metric, according to recent census data (www.census.gov), the U.S. will continue to be the principal receiving country of linguistically diverse immigrants, especially from the Caribbean and Latin America. As a consequence, U.S. public schools will be charged with the task of educating school-age immigrant children from this region whose language and literacy needs will challenge traditional paradigms, research, and practice with respect to the nexus of language, literacy, and culture. Although a signiﬁcant body of work has examined the educational needs, issues, and academic performance of Spanish-speaking children from the Caribbean and Latin America in U.S. schools (Farr, 2005; García & Menken, 2006; Torres-Guzmán et al., 2002; Valdés, 2001, among numerous others), research on the language, literacy, and culture of children from the English-speaking (Anglophone) Caribbean1 in North American schools has been far less widespread or more regionally focused (Clachar, 2004a, 2004b; Coelho, 1991; Nero, 2001, 2006; Pratt-Johnson, 2006; Winer, 2006). The research on the latter reﬂects the settlement patterns of Anglophone Caribbean immigrants, who are disproportionately located on the east coast of the U.S., speciﬁcally New York City (home to the largest Anglophone Caribbean population outside of the Caribbean), New Jersey, Maryland, Washington, DC, Atlanta, and Miami. However, as immigration from the Anglophone Caribbean continues to increase exponentially, and shows no signs of abating, it will become necessary for educators to deepen understanding of the language and literacy issues of this population, as teachers grow more likely to encounter Anglophone Caribbean children in their classrooms in other parts of the U.S. and Canada. This chapter attempts to add to that understanding by exploring the language of the majority of recent immigrants from the English-speaking Caribbean, hereafter called Caribbean Creole English (CCE);2 the extent to which their language practices impact their literacy development in school; and the degree to which teacher training and professional development in sociolinguistics as well as the history, structure, and use of CCE might inﬂuence pedagogical approaches in order to enhance the literacy development of CCE speakers.