This article aims to examine how and why we can use digital storytelling (DST) to teach literature in the upper secondary classroom, and makes use of Mark Haddon’s complex, multimodal novel The Curious Incident of the Dog in the Night-Time (2004) as an example. DST is a powerful tool for the 21st century classroom, with the potential to help pupils to become empathetic, creative, inquisitive and critical thinkers. When applied to literature, DST allows pupils to continue the literary text in creative ways by making their own digital story using a basic video editing application such as iMovie or Microsoft Bilder. Such literature-based DST (LDST) distinguishes itself from ordinary DST use in school. The values, qualities and peculiarities of literature offer an imaginative point of departure for new ways of using digital media in school. The Curious Incident is an exceptionally appropriate novel to use with DST, because the novel and the method share numerous features, not least multimodal ones. The narrative structures and aesthetic dimensions of the novel overlap with characteristics of DST. Furthermore, the many hermeneutic dimensions of Haddon’s novel can also be explored by the imaginative possibilities of DST. The definitions and interrelations between literature, text and modality are discussed throughout the article with reference to both philosophers and school didacticians. LDST is remarkable in the way it encourages pupils to sympathise, to interpret, to think critically and to develop their own imaginative ability and language skills. This article argues that LDST is useful in upper secondary education by examining the corresponding educational qualities and possibilities of Haddon’s multimodal novel and DST, and by drawing upon the new education reform in Norway articulated in the Core curriculum of 2020 and the Curriculum in English. Furthermore, the article concludes with the presentation, analysis and assessment of a pilot LDST-project conducted in an upper secondary school in Troms County as part of an MA lector thesis at UiT The Arctic University Norway. Thus, this article’s wider aim is to bring new research perspectives to English education, with a special focus on the use of literature and active forms of learning.