Twenty-first century education includes dynamic learning that is complicated by interactions in both fixed and protean virtual spaces, and it is important to consider the degree of power, agency, and awareness students have as producers and consumers of interactive technology. Outside of school, students engage in meaning making practices, and media, such as video games and websites, embrace certain "technologies of power"--space, surveillance, and documentation (Foucault, 1977)--to shape consumers' thinking and behavior. This article calls attention to the role of students and media executives in the development and maintenance of power structures, presenting new understandings of students' interactions with virtual texts and the producers'/designers' critical influence in shaping literacy experiences. Data from a three-year longitudinal study of thirty media producers of sites, such as Club Penguin and MyPopStudio, and an eight-month study of four adolescent gamers and their video game playing both reveal regulatory measures that promote and constrain student-navigated literacies. Understanding the dynamics of these virtual spaces and how they regulate and create a learning culture that hinges on collaboration and communication, educators can capitalize on the cooperative skills students develop and help students hone a critical sensitivity and understanding of their digital literacies.