This paper presents the findings of a research project that sought to interrogate the possibilities of digital storytelling as a pathway towards a more complete understanding of treaties and the treaty relationship in western Canada. This research is situated in the province of Saskatchewan, where treaty education (that is, education about the history of the numbered treaties signed between First Nations people and the British Crown, as well as the subsequent history of the treaty relationship) has been mandatory for almost a decade. The paper details a two-year journey alongside elementary educators as they used digital storytelling to take up treaty education in their classrooms. We present an overview of the research project as well as the narratives of a teacher, a researcher, and a Cree knowledge keeper, all of whom were involved in and reflected on the research journey. We consider the research findings alongside these narratives in order to explore the possibilities that digital storytelling might offer as we, as a Canadian nation, move towards reconciliation with Aboriginal people within a Canadian context of ongoing colonialism.