Drawing on the lived experiences of high school-aged young Black immigrants, this book paints imaginaries of translanguaging and transsemiotizing, leveraged transnationally by teenagers across the Caribbean and the United States. The Black Caribbean youth reflect a full range of literacy practices – six distinct holistic literacies - identified as a basis for flourishing. These literacies encapsulate numerous examples of how the youth are racialized transgeographically, based on their translanguaging and transsemiotizing with Englishes, both institutionally and individually. In turn, the book advances a heuristic of semiolingual innocence containing eight elements, informed by the Caribbean youth's holistic literacies. Through the eight elements presented -- flourishing, purpose, comfort, expansion, paradox, originality, interdependence, and imagination – stakeholders and systems will be positioned to better understand and address the urgent needs of these youth. Ultimately, the heuristic supports a reinscribing of semiolingual innocence for Black Caribbean immigrant and transnational youth, as well as for all youth.