A range of recent academic, policy and practice-focused work in the UK and internationally has identified a need for more focused attention on the role of digital literacies in enabling young people to more effectively navigate their way through an increasingly complex, digitally mediated world. In this article, we explore the main debates taking place around the prevalence of digital media in the early twenty-first century, with emphasis on the role of pervasive digital media in educational settings. Focusing on the practice-based project, Digital Commonwealth, a series of critical insights are drawn, highlighting the difficulties facing educational authorities and young people in dealing with the opportunities and threats brought about by digital media. We conclude that a critical digital citizenship agenda needs to be embedded in educational narratives, where young people are, through practice, asked to ponder how digitally mediated publics operate in the school setting and beyond. Integrating 'making' and 'thinking critically' about the benefits and dangers of pervasive digital media in and outside of school is imperative. Our study suggests that there remain significant inequities in terms of provision across schools, access to suitable infrastructure and equipment, and the presence of qualified and confident staff with the requisite digital leadership attributes to enable digital media projects to be integrated into everyday learning practices. Major events, like the Commonwealth Games, can precipitate and accelerate uptake of new approaches and innovative thinking but they do not represent a panacea for the systemic development of critical digital citizenship over time.