The recent "global turn" in Rhetoric and Composition has increased our attention to multi-cultural, multi-lingual, and multi-literacy education and to the need for pedagogy that accounts for cultural, linguistic, and material diversity. Scholarship suggests rhetorical and linguistic dexterity as a primary means for students to participate across a range of situations and modalities. While promoting these pedagogies and discourses of dexterity is beneficial, little attention has been given to the frictions involved in such movements. This dissertation, therefore, looks to the thornier points of dexterity from a global perspective by evoking a theoretical framework that foregrounds the processes and structures that inhibit easy and dexterous transitions between situated sites while also emphasizing the creative responses to such international movements. I describe this as transnational literacy: a series of inventive strategies that negotiate the interplay between exclusionary ideologies, the discursive resources that rhetors bring, and a particular local context. Drawing on textual and qualitative analysis of Third Culture Kids, I suggest that these efforts to reposition—which take place within a complex array of shifting local, national, and geopolitical contexts—must confront a complex web of hurdles that reject the possibility of negotiating and realigning across contexts, but can nonetheless proceed to question, transform, and innovate these impasses. Taken together, these characteristics capture a core feature of transnational literacies: frictive dexterity. From this amended notion, neither friction nor dexterity is the principle mark of boundary-work. Rather, it is the dynamic tensions and fits and starts between these two rhetorical possibilities that become the base from which to construct a literacy-based, problem-solving pedagogy responsive to twenty-first century needs.