During the last and current century, the United States has witnessed an increasing upward trend in immigration from the racially and linguistically diverse English-speaking or Anglophone Caribbean (Lorenzi & Batalova, 2022). However, there needs to be more research on Afro-Anglophone Caribbean (AAC) students recounting their experiences in schools in the United States. Framed by a raciolinguistic perspective and post-colonial theory, this qualitative study captures the experiences of seven (7) student participants from four (4) academy high schools in an urban school district in the U.S. Northeast, who provided insights into their linguistic identities and experiences in high schools in the United States. This 2-year qualitative study highlighted the enduring nature of raciolinguistic ideologies prevalent in homes and schools. This study also strengthened ideas of multilingualism and reminded us of the need for school norms to become more inclusive and tolerant of diversity.