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The development of electronic monitoring policy over the last decade in Scotland has contributed towards its expansion and the intensification of what McNeill (2019) refers to as mass supervision. Often posited as a solution to relieve problems in the criminal justice system such as prison overcrowding and high remand populations, electronic monitoring can be punitive and problematic, exposing more people to diffused forms of social control and functioning more as a supplementary feature of prisons as opposed to a substitution for prisons. In this chapter, I explore the existing and emerging policy landscape of penal electronic monitoring Scotland, drawing upon qualitative, experiential data about being subject to and enforcing penal electronic monitoring in Scotland (see Casey, 2021) to highlight how policy is enacted in practice. Ultimately, I argue that there are fundamental issues with how electronic monitoring is currently enacted in terms of what it promises, in terms of fairness and in relation to the potential harms of integration. I call for a fundamental and holistic reframing of policy and regulation of penal electronic monitoring in Scotland that avoids siloed approaches towards policymaking, attending to both the social and digital impacts of electronic monitoring in people’s lives, thus contributing to arguments about how ‘mass supervision’ should be moderated and resisted.