The clichés "it's a small world" and "the world is our classroom" are becoming practical realities for many educators. Increasingly accessible transnational contexts for English language teaching and learning offer new opportunities for local-global learning. This article reflects on a content-based online English course focused on community youth leadership that was offered for Brazilian teens by U.S. instructors and graduate students. The researchers used the backdrop of English learning focused on key concepts to engage students in critical self-reflection, collaborative discussion with peers, and civic engagement with their home communities. This course focused on communication skills, content knowledge, and technology practices needed for young adults to engage each other as emerging global citizens. Students wrote reflections on identity, planned and reflected on community interviews, and designed community-based service projects. The authors describe how students and instructors used a variety of formal and informal communication platforms to experiment with the language and communication strategies students needed to get beyond simple vocabulary practice and into meaningful discourse about contested concepts such as identity, community, social responsibility, social hope, leadership, and beliefs. The authors discuss how students creatively used English across multiple online platforms and geographic borders to reimagine and project themselves as agents of positive social change and emerging community leaders.