Digital technologies are an important requirement for curriculum expectations, including general ICT capability and STEM education. These technologies are also positioned as mechanisms for educational reform via transformation of teacher practice. It seems, however, that wide-scale transformation of teacher practice and digital learning remain unrealized. This is commonly attributed to a range of challenges associated with extrinsic and intrinsic influences, which while acknowledged, are not well conceptualized. Using evidence from a case study of teachers working to transform their practice with digital technologies, this paper presents a tri-theory framework that was used to conceptualize these challenges. Activity Theory provided a mechanism for teachers to identify extrinsic influences in activity systems then contextualize and reduce the perceived significance of challenging contradictions. System 1 and System 2 Thinking Theory was used by the teachers to explore the role of routine, attitudes, and beliefs in their practice and conceptualize discomfort associated with changes in practice. Transformative Learning Theory is presented as a mechanism to explain the interaction between extrinsic and intrinsic influences during the teachers' collaborative attempts to consciously transform their practice. As a common language for discourse, the tri-theory framework allowed the teachers to collaboratively contextualize challenges of realizing digital learning.