Deeply integrating digital technologies in pedagogy and learning is associated with changes in classroom roles, relationships and actions that can challenge established teacher routines. This paper presents the findings of an eight-month case study of teachers transforming pedagogy to enact their design for personalised digital learning. Participating teachers reported that established classroom routines for managing behaviour and monitoring student engagement were challenged, and along with changes in classroom roles, this resulted in disorientation and uncertainty, but also created opportunities to consider new routines. This paper proposes that Dual Systems theory can be used to conceptualise the role of routine in teacher practice and the emergent challenges of transforming pedagogy with digital technologies.