This short article examines how the mutual shaping of gender and technology can contribute to the reproduction of racialized class divisions. The article is based on an in-depth ethnographic study of the launch of a progressive New York City public middle school. The school aimed to integrate twenty-first-century digital technologies and skills into the curriculum while promoting student-centered learning and social equity. The article argues that educators and privileged parents constructed an educational context that facilitated and legitimized students who enacted masculinities rooted in video game culture even as it disciplined and purged students who enacted masculinities rooted in more canonical forms of boy culture. In doing so, the school paradoxically helped perpetuate the racialized class divisions that it hoped new media would help it overcome.