This paper offers a critical discussion on voice and representation in youth digital media production in educational settings. The paper builds on existing calls from digital media and visual studies scholars to approach youth-made media with greater attention to context in production practices. In this discussion, the author addresses the importance of technological tools, media genres, settings, and program design in the construction of voice and representation for children and youth making digital media. The paper presents a case study derived from a three-year ethnographic research project and feminist intervention in one under-resourced school in Toronto, Canada. Through the examples presented in this paper, the author presents a critical discussion about the process and content of digital video created by girls making media in particular contexts, under distinct conditions.