In this chapter, I begin by complicating how Black immigrants’ perception as a ‘model minority’ in the US creates a challenge for equitably engaging with their literacies and languaging as a function of schooling. Joining the conversation on immigrant and transnational literacies, I present foundational language and literacy research in the US that has functioned as a backdrop against which Black Caribbean immigrants’ literacies and languaging are considered. To situate Afro-Caribbean languaging, Englishes, and literacies within its broader contexts, I then discuss education, migration, and cultures across the Black diaspora addressing the historical and contemporary educational landscape of Black people in the Caribbean. I further accomplish this situational placement of Afro-Caribbean languaging, Englishes, and literacies through a discussion of the historical and contemporary socio-educational landscape of Black immigrants in the US. Through this broadly painted portrait operating at the interstices of the educational, racial, historical, social, linguistic, and religious domains in the lives of Black Caribbean peoples and specifically youth, this chapter serves as a nuanced and contextual backdrop against which to understand the analyses of Black Caribbean immigrant youth’s language and literacies presented in this book.