Digital storytelling (DST) has been widely used as a means of empowerment for marginalised voices across community-based projects worldwide. This paper discusses uses but also limitations of the practice in the context of a Melbourne-based youth media program for ‘youth at risk’ called YouthWorx. Based on our ongoing, long-term ethnographic research, we explore the cultural production of digital stories as a co-creative process that exposes a range of controversies to do with the politics of ‘voice’, genre’s communicative potential and ethical considerations. Concrete examples from YouthWorx’s pedagogical work serve to illustrate the values of self-expression (‘voice’), critical reflection and collaboration that form part of broader social transformations generated by these creative practices. The critique of DST practice offered here connects with existing studies concerned with the socially contextualised processes of media education, and the theoretical shift beyond ‘the right to speak’ towards ‘the right to be understood’ (Husband, 2009). The paper recommends more analytical attention be paid to a dynamic social process of learning (of media, interpersonal competencies) and community-building, extending beyond the immediate DST situation, rather than narrowing the focus on end-result atomised media products.