The purpose of this thesis is to investigate a pedagogical strategy in the teaching of English: namely, the use of transnational collaboration, via digital communication tools, between English writing classrooms to expand their study of rhetoric. My core argument is that when students are working with geographically disparate students (and peer reviewers) online, they can be shown to be uniquely invested in critical thinking and as a result, their analyses of rhetoric. As a case study, I focus on a 2014 project that I built at Stony Brook University in New York, in collaboration with English instructors working in Kandahar, Afghanistan and Quito, Ecuador. I use a mixed-method, qualitative approach to communicate examples and findings. Pointing to the results of our 2014 project, I first discuss why the students in this case study were uniquely engaged in critical thinking when digitally collaborating-both with one another and the two distant classrooms. Then I identify how English instructors can create spaces for transnational relationships in their pedagogy. I build an argument that it is time for critical pedagogy in the English classroom to incorporate a more thoughtful practice of digital collaboration now that we have the tools available to us. The method I suggest here, through my own experience with my students, is simply connecting and setting up written collaboration between classrooms. Transnational collaboration among classrooms is an effective pedagogical practice, but it is also an ethical one. Connecting classrooms enhances students' critical thinking. But it is also a newly viable method to fulfill our duty as critical pedagogues. I support this argument with Paulo Freire's and bell hooks' writing on critical pedagogy, John Dewey's definition of critical thinking, and the work of Ethan Zuckerman's writing on the internet's simultaneous failure and potential to foster global connectedness. At the close of this thesis, I broaden the scope of the argument beyond the classroom. I discuss my belief that it is not only our duty as critical pedagogues to create spaces for transnational collaboration and relationship, but even more, that this practice fits into a larger spectrum of ways that people can foster connectedness, respect, and investment in the well being and growth of others. That projects like these, new in technology, but old in teaching philosophy, can help make the world a more equitable and just place. Teachers like Paulo Freire, bell hooks, and many others have long advocated for this in their work. In 1976 Freire wrote that education is "the practice of freedom" (Freire). hooks responded to Freire in 1994, writing that transgression-a movement against and beyond boundaries-is what makes education the practice of freedom (hooks). My hope expressed in this paper is that whether in the classroom or in any other space, we prioritize transgressing boundaries over staying in silos-prioritizing critical engagement, prioritizing relationship, and prioritizing one another.