This article uses insights from media and communications research over recent decades to inform a critical analysis of the burgeoning multidisciplinary study of youthful digital engagement. The analysis first points to the systematic connections between mediatization and the problematic dimensions of consumerism, individualization, and globalization. Critiquing the popular rhetoric of the digital native, it then draws on empirical observation to temper excessive celebration of youthful creative and expressive skills and, thus, support rather than undermine the resourcing of digital opportunities for youth. To identify future directions for research on the social uses and consequences of digital media, the author argues that instead of asking, narrowly, how the digital impacts on learning or participation, we should turn the question around to identify the wide array of factors that shape learning and participation to reveal when and how the digital fits within this. The changing balance in childhood between independence and dependence positions digital media, for at least some young people, as a valued opportunity to explore, learn, and participate. But the consequent intertwining of opportunity and risk in the digital environment means that youth pursue the latter as well as the former in a manner here termed “playing with fire.” Although disapproved of by adults, such activities may nonetheless benefit learning, participation, and resilience. The article concludes by observing some key dilemmas for a future policy-relevant agenda that will demand critical reflexivity from researchers if they are to navigate between independence and engagement.

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