Digital technologies are a part of schooling, however, given the significant focus on using of digital technologies in teaching and learning, there is little evidence of wide scale transformation. It is within this context that this paper reports on a qualitative, explanatory case study of six teachers, with experience in enhancing pedagogies in a well-established ubiquitous technologies environment, consciously seeking to transform their practice to enact personalized digital learning. The findings indicate three interacting factors contributed to the degrees of transformation: teachers' frames of reference (beliefs and attitudes), habits of mind (prior experience), and modes of transformative learning. This paper highlights how diversification of classroom roles, relationships and actions created challenges for teachers with experience integrating digital technologies in teaching and learning.