The large-scale ongoing migration of Anglophone Caribbean natives to North America, particularly to New York City, in the last two decades, has brought an influx of Caribbean English (CE)-speaking students into US and Canadian schools and colleges. This article discusses the extent to which such students, who publicly identify themselves as native speakers of English but whose variety of English is often misunderstood by North American teachers, challenge the latter to examine their tacit assumptions about the English language, ownership of English, and linguistic identity. The author provides examples of commonly used features of CE that are likely to create misunderstanding in American classrooms. She argues that teachers of Caribbean English speakers will need to explore new paradigms for language placement, assessment and development, and finally proposes an agenda for responding to the linguistic and broader educational needs of CE-speaking students.