Teachers are increasingly required to enact assessment policies in digitalised spaces, raising ethical issues of privacy and surveillance in the process. Yet, while "policy enactment" has been examined extensively, there remains research uncertainty around the ethical dimensions associated with assessment policy in digitalised settings. Drawing upon Ball et al.'s Typology of Policy Positions, and utilising Australian teachers' interviews, we illustrate how the policy positions of the latter were shaped by "critical ethical incidents" in digitalised conditions. We describe how teachers struggled to reconcile their ethical obligation to provide valid assessment outcomes with their "duty of care, procedural institutional commitments," and the need to protect "student privacy." To ensure 'ethical assessment' practices that best fulfil their obligations, the educators were not confined to one policy position, rather they moved across roles, also framed as moral recuperation mechanisms. Regulations to help facilitate policy enactments of 'ethical assessment' in digitalised contexts are suggested.