Digital storytelling involves the creation of short, personal narratives combining images, sounds, and text in a multimedia computer-based platform. In education, digital storytelling has been used to foster learning in formal and informal spaces worldwide. The authors offer a critical discussion of claims about digital storytelling's usefulness for supporting various types of learning and conceptualize it as a context rather than a tool. Drawing on examples from digital storytelling workshops, their research team has designed for Secondary English classrooms in Singapore, the authors discuss the role that digital storytelling as an interactive digital media (IDM) context can have in shaping youths' opportunities to be active authors and participants in a media production culture, which is a growing focus of education across the globe. Wrapped up in ideals of 21st century learning, digital literacies, and new media lies a dual mandate to resonate with and draw upon youths' everyday media practices as well as foster critical thinking dispositions, and the authors offer brief recommendations to these ends as they relate to digital storytelling-as-context and the learning sciences.