Online exam supervision technologies have recently generated significant controversy and concern. Their use is now booming due to growing demand for online courses and for off-campus assessment options amid COVID-19 lockdowns. Online proctoring technologies purport to effectively oversee students sitting online exams by using artificial intelligence systems supplemented by human invigilators. Such technologies have alarmed some students who see them as a “Big Brother-like” threat to liberty and privacy, and as potentially unfair and discriminatory. However, some universities and educators defend (...) their judicious use. Critical ethical appraisal of online proctoring technologies is overdue. This essay provides one of the first sustained moral philosophical analyses of these technologies, focusing on ethical notions of academic integrity, fairness, non-maleficence, transparency, privacy, autonomy, liberty, and trust. Most of these concepts are prominent in the new field of AI ethics, and all are relevant to education. The essay discusses these ethical issues. It also offers suggestions for educational institutions and educators interested in the technologies about the kinds of inquiries they need to make and the governance and review processes they might need to adopt to justify and remain accountable for using online proctoring technologies. The rapid and contentious rise of proctoring software provides a fruitful ethical case study of how AI is infiltrating all areas of life. The social impacts and moral consequences of this digital technology warrant ongoing scrutiny and study. (shrink)