This paper uses a third-generation Activity Theory perspective to gain insight into the contradictions between the activity systems of the physical and virtual high school classroom from the perspective of teachers who had transitioned from one system to the other. Data collection relied on semi-structured interviews conducted with e-teachers as well as management/support personnel of an organisation charged with delivering web-based high school courses in the Canadian province of Newfoundland and Labrador. Contradictions related to time and workload, physical presence, interaction and rapport building, and use of direct messaging and email. The contradictions can be explained by a difference between the mediating tools in each activity system. The absence in the virtual classroom of body language and visual presence as mediators requires e-teachers to find new ways of interacting and building rapport and necessitates a shift from a practice of controlling to engaging students' attention.