Creating authentic contexts for our teacher candidates to learn about ELT in transnational contexts has become increasingly important for the depth of learning it affords as boundaries begin to blur in this transnational world. In this chapter, I present our work in developing and teaching an online Business English program for Kenyan youth, who were part of a non-profit organization with a mission to help homeless youth escape poverty through the provision of professional development opportunities. Through the process of engaging in this transnational context, our teacher candidates became more cognizant of the conceptual understanding of the historical, political, economic and social influences impacting the process of language teaching and learning within this context. Preparing English teachers to teach in this transnational context allowed for critical conversations around power, language hierarchies, ownership of English, and post-methods and post-structural perspectives on language teaching. It also provided a space for our teacher candidates to continually examine and negotiate their positionality as English teachers within this transnational context