In participatory cultures, the lines between producers and consumers of text are blurred, and communities emerge that are based on shared interest and peer support. Although literacy scholarship has mostly focused on youth engagement and literacy practices within online participatory cultures, scholars in the learning sciences investigate these ideas through connected learning. This article explores bringing connected learning principles into English classrooms and examines how one high school, partnering with the National Writing Project, redesigned their senior English course and senior capstone project around connected learning. The authors highlight its design and share students’ experiences with the project to illustrate the possibilities and tensions around designing for such a project in school settings.