In this chapter, we present a case study of video-based monitoring (VbM) for proctoring online exams. The use of VbM grew significantly during the pandemic. As the use of VbM has increased, so have the questions regarding its usefulness and capacity for surveillance. Like many educational technologies, the use of VbM presents a paradox where the efficiency and convenience of assessment come at the expense of privacy and control. In this chapter, we assess the technological paradoxes surrounding the use of VbM. We draw on our personal experiences as well as the literature. Our analysis highlights the complexity of using new AI-based platform technologies. We discuss whether the infusion of a technology such as VbM can serve as an occasion for restructuring teaching practices in a meaningful way and has the potential to ignite an ethical and moral imagination among faculty in regard to technology use.