This case study examines the learning, identity and language development experienced by "overage" 8th-grade students who have been left behind two or more years in their New York City middle school and are participating in an extended-day video documentary program. The students practise a range of literacy skills naturally embedded in the documentary production process. The topic they have chosen to explore through their video project is teen sex. This program seeks to create a vibrant and active learning space that is planting the seeds for what might grow into a sustained program of youth-generated media in their school. Observing and listening in on the students in this case illustrates practical applications of learning theories including multiple discourses, double abstraction, situated learning, and cognitive apprenticeships and proposes new possibilities for literacy development with low-performing students as well as the kind of hybrid informal/formal learning environments needed to support such development. (Contains 1 footnote.)