The purpose of this paper is to highlight the evolution of privacy, as we enter a world of amplified surveillance. Proctoring technology is a software-based tool that is being implemented at post-secondary institutions. We will explore some of the key issues of its framework in relation to student privacy and academic integrity. As remote learning and exams become more mainstream, post-secondary schools want to ensure that their students are not completing exams in a dishonest fashion. We will look at the ramifications for both parties, students and institutions, to determine if there is a breach of privacy. The recording and storing of personal data have implications with privacy law and the human rights code. We want to explore the ‘big brother’ aspect of this technology and how post-secondary institutions are putting their students in an awkward position; conform or withdraw. Those who want to get a post-secondary education are subjected to data scrutiny in an unprecedented manner. Allowing post-secondary schools to hire third party private companies in order to gain access to student’s personal devices allows for a large window of privacy concern. The significance of the study is to raise awareness and find reasonable solutions to these concerns.