In this longitudinal case study, Catherine Compton-­Lilly and Margaret R. Hawkins explore one immigrant youth's engagement with transglobal activities and flows of information and his emerging awareness of the world. Contending that transglobal flows create learning opportunities that are rarely available to children raised in mononational and monocultural spaces, the authors add to scholarship that highlights the knowledge, awareness, understandings, and literacies that children in transglobal families bring to class rooms. Specifically, they exam ine twelve years of longitudinal data following the youth's development of a critical cosmopolitan stance and then apply a transliteracies framework to analyze complementary facets of emergence, uptake, resonance, and scale implicated in transglobal relations and comparisons. The article closes with recommendations for educational practice.