Professor Lee Shulman (1987b) introduced a view of teaching that encompassed a series of six steps: comprehension; transformation; instruction; evaluation; reflection and new comprehension, which he termed pedagogical reasoning. He suggested an image of teaching as the exchange of ideas from the teacher, who must comprehend an idea to be able to shape and tailor it, in order for the student to grasp and understand the idea. This complex interplay of judgment and action is at the heart of pedagogical reasoning. Since 1986, there have been very few published research studies that have either tested or reported the use of Shulman’s Model of Pedagogical Reasoning and Action to describe the realities of teaching. It could be suggested that many researchers could not move beyond referring to Shulman’s other important contribution in proposing pedagogical content knowledge (PCK). What they seemed to have missed was how Shulman proposed that PCK was developed through the processes of pedagogical reasoning. Shulman provided limited insight into the teachers studied as part of the Knowledge Growth in Teaching project undertaken at Stanford University. Those teachers were described in limited vignettes where Nancy, Colleen, Judy, Alan, George and Frank (Shulman, 1987b; Shulman & Sykes, 1986; Wilson, Shulman, & Richert, 1987) were portrayed to help in understanding the intricacies of pedagogical reasoning. This study attempts to revisit Shulman’s original work to understand how current teachers pedagogically reason, and, in particular, to understand the impact of digital technologies on their pedagogical reasoning. This research project used Shulman’s view of teaching as a theoretical starting point to pose the question: How do teachers pedagogically reason with digital technologies?