In Ireland, as with many international jurisdictions, digital technology is firmly positioned at the core of educational discourses. However, despite a rise in ‘techno-positivity’ among professionals in schools, these positive attitudes do not seem to permeate through to practice nor in effective learning outcomes. As a result, given the introduction of the Digital Learning Framework in the Irish schooling system, this study focuses on the initial experiences of those who lead the initiative within their respective schools and the contextual nuances they must navigate in the design of the enactment. This qualitative study comprised in-depth interviews with the Digital Learning Leaders of 10 different schools. Data evidenced the initial organisational considerations a leader must reckon with during the planning phase, and early indications of pedagogical impact, leading to a conclusion regarding contextual literacy. The research also highlights the subtle policy shift of embedding digital technologies within school evaluation mechanisms, heightening a sense of accountability associated with successful enactment.