How do youth use media and technology as they learn to be participants in civic and democratic practices? We share two case studies—one from a media arts production organization and one from a school board youth group—that revolve around youth-adult interactions in learning environments that offer youth real opportunities to be influential in their respective communities. The cases feature youth and their involvements with digital media, pedagogical approaches, and engagements that enhance their participatory capacities. There are multiple channels through which these interactions happen, some with and facilitated by adults and others created and negotiated by youth. We describe how youth and adults establish learning environments for each other, negotiate the grounds for participation, and explore the possibilities and limitations of social and digital technologies in these processes, supporting the idea that this learning is something that young people do as agents in their development.