This chapter examines the language, identities, attitudes, and pedagogical implications that arise from the presence of a rapidly increasing number of Caribbean Creole English (CCE) speakers in North American schools and colleges. CCE speakers publicly self-identify as native speakers of English only. Yet, many teachers’ encounters with the spoken and/or written language of CCE speakers lead them to question their students’ nativeness as speakers of English, and the very notion of what counts as English. On the other hand, non-Caribbean students’ responses to encounters with CCE speakers range from questioning their English, to accepting it, to selectively “borrowing” from it for identity affiliation (Rampton 1990). Using data from CCE speakers in one New York City public school as a case study, the author explores teachers’ and students’ varied linguistic responses to CCE speakers. Taking a plurilingual stance, she argues that the contact between CCE and other varieties of English is already changing classroom English; calls for a re-examination of the assumptions and goals of school-based language practices, and for utilizing CCE as a point of departure for pedagogy, literacy development, and raising language diversity awareness. Recommendations for teacher training and classroom instruction are also offered.