This article examines academic cheating in Egyptian secondary education at a time of assessment fetishization, educational digitalization and pandemic exceptionalism. It shows how, while promising a tighter grip on assessment, digital technologies afforded a new modality of cheating with a scale and speed unprecedented in Egyptian educational history. Using longitudinal interviews with educational communities and qualitative social media research to observe cheating in situ, this article traces the emergence of digital collective cheating, the unsanctioned collective assistance during examinations using digital technologies, on social media third spaces. In addition to embodying a collaborative ethic between students, digital collective cheating served as a form of collective resistance to state-led digitalization and unfair structural conditions. By examining the empirical realities and unintended consequences of digital technologies in assessment, the Egyptian case highlights the dangers of, and serves as a cautionary tale for, unbridled technological utopianism, solutionism and inevitablism in education.