Much recent scholarly investigation has been focused on the promise of digitalization and the new ways of working and organizing it makes possible. In this paper, we analyze how the COVID-19 pandemic has acted as a natural breaching experiment that has challenged taken-for-granted expectations about digitalization and revealed four important issues: uneven access to digital infrastructures, the persistence of the analog in digitalization, the brittleness of unchecked digitalization, and panoptical surveillance. The sudden shift to digital work has exposed taken-for-granted assumptions about the universality of digital access. The crisis has also revealed that many highly digitalized processes still rely on analog elements. The pandemic has also exposed that many algorithms used in digitalized inter-organizational processes are brittle due to overreliance on historic patterns. Finally, the pandemic has breached fundamental expectations of privacy when organizational surveillance was extended into private and public spaces. Thus, the pandemic has laid bare fundamental challenges in digitalization and has exposed the limits of rose‑tinted thinking about the relation between technology and organizing.