As resources become available, the tools of digital storytelling are being introduced into a wide variety of contexts, with new projects involving youth emerging in increasingly remote areas throughout the developing world. In 2008, the Sonke Gender Justice Network teamed up with the Center for Digital Storytelling’s Silence Speaks initiative to work with a group of rural youth in Eastern Cape, South Africa. The results of this project are eight digital stories by young Xhosa people that capture the challenges they face and the futures they yearn for in post-apartheid South Africa. By exploring the success and challenges of the project, we show the potential that thoughtfully designed digital storytelling efforts offer as both a psychological outlet and a tool for community education and social activism with marginalized youth.