Many school districts have encouraged movement from traditional classrooms and teaching strategies to strategies that employ the Internet and educational technology (Ed Tech). The transition to Internet-based Ed Tech has many benefits, such as reduced costs for institutions and greater convenience for students and instructors alike. However, this convenience comes at great expense as Ed Tech is often implemented with little thought to students’ education. This study adopted a philosophical inquiry approach to address concerns related to the implementation of the Internet-based Ed Tech in teaching. It begins by critiquing Ontario’s public policy around the procurement of Ed Tech and the use of e-learning strategies with some reference to other educational jurisdictions. It then discusses privacy issues and risks surrounding the use of Internet-related technologies in education, as well as changes in the relationship between students and teachers as education moves from the traditional classroom to the e-learning environment. Finally, the study critiques theories of education that support e-learning and shows that their implementation limits the transformative nature of education as defined by Gert Biesta.