This study follows three secondary teachers as they facilitate a digital storytelling project with their students for the first time. All three teachers were not specifically trained in digital storytelling in order to investigate what happens when a digital storytelling novice tries to do a project like this with his or her students. The study follows two high school English teachers and one middle school math teacher. Each teacher's experience is shared in a case study, and all three case studies are compared and contrasted in a cross-case analysis. There is a discussion of the types of projects the teachers conducted and any challenges they faced. Strategies to overcome the challenges are also included. A variety of assessment rubrics are included in the appendix. In the review of literature, the history of digital storytelling is illuminated, as are historical concepts of literacy. There is also an exploration of twenty-first century skills including multiliteracies such as media and technology literacy. Both the teachers and their students offer suggestions to future teachers taking on digital storytelling projects. The dissertation ends with a discussion of future scholarship in educational uses of digital storytelling.