Founded on the philosophy of the constructivist and collaborative pursuit and production of new knowledge, pedagogy is at the very heart of Digital Humanities (DH). However, among the challenges for the institutionalisation of DH pedagogy, particularly in literature departments, is a dearth of sufficient literature on DH pedagogy—a concern echoed in “Where’s the Pedagogy?” by Stephen Brier (2012) among other scholar-practitioners of DH. As Hirsch (2012a) points out, the focus of the literature is predominantly “on the theories, principles, and research practices associated with the Digital Humanities—past and present—and not on issues of pedagogy”. Teaching is often “bracketed off” as an afterthought in the discussion on DH, which is a reflection of the practical realities of DH studies, particularly in literature departments. Hirsch argues that the bracketing off or complete exclusion of pedagogy in critical discussions of the Digital Humanities, as is often the case, reflects, and reinforces, the conflicting contrast between teaching and research of DH in academia. The chapter highlights the discrepancy between traditional pedagogical approaches prevalent in literature departments, especially in India, and the collaborative, hands-on methods intrinsic to DH practice. Traditional approaches often focus on the delivery of content from teacher to student, whereas DH emphasises inquiry-based learning, experimentation, and collaboration among peers and instructors. In the context of DH, a “pedagogy of digital experimentation” involves students actively engaging in making and doing, mirroring the work of DH professionals. This approach encourages collaborative exploration and discovery, aligning with the core tenets of DH, such as practice, discovery, and community. However, many literature departments are not prepared to embrace this approach, which involves what Ramsay (2010/2014) terms “screwing around” or “surfing and stumbling” as part of the research methodology. Shifting towards a pedagogy of active experimentation requires a significant paradigm shift, challenging traditional notions of teaching and learning. This shift may lead to discomfort or uncertainty for both teachers and students as they navigate unfamiliar territories. Bonds (2014) suggests that this discomfort arises from the need to co-produce knowledge in a constructivist manner, rather than passively receiving it. To bridge the gap between traditional pedagogy and DH practices, there needs to be a re-evaluation of entrenched ideas about teaching and scholarship. This re-evaluation should challenge limited perceptions of the teacher’s role and the connection between teaching and scholarship. Without this re-evaluation, Digital Humanities risks being confined to superficial applications like computer-assisted text analysis, rather than realising its full potential in higher education. Bringing pedagogy to the forefront of Digital Humanities in literature programs requires a fundamental reconsideration of educational practices and the roles of teachers and students. Embracing collaborative, experimental approaches can pave the way for the integration of DH into mainstream educational frameworks, fostering innovation and deeper engagement with humanities disciplines.