This chapter examines the ways in which transnational identity and social networks are reflected in classroom languaging practices in settings where students speak Caribbean Creole English. Microethnographic discourse analysis of interactions between a Jamaican secondary student in New York City and her English teacher reveal that the student produces writing and interacts with her teacher through a multidialectal repertoire, drawing on multiple varieties of English that reflect her simultaneous participation in Jamaican, African American, and public school communities. The student’s languaging affirms her transnational identity while defying monolingualist and standard language ideologies. Shifts in the teacher’s instructional practices demonstrate the potential of professional development on students’ heterogenous language use.