In light of the Covid-19 pandemic, it is often assumed that working at home represents a fundamental transformation in the way managers work. But is managerial homeworking that new? To answer this question, we draw on labour process theory and three empirical studies to place post-pandemic homeworking in historical sociological perspective. Overall, we find that homeworking is not a novel phenomenon, but has been driven by various logics. Explaining these, we contend initially that recent studies of managers working at home have focused on the mandated temporal present of the practice under Covid-19, which has resulted in homeworking being portrayed idiosyncratically. In contrast, and to attain a more comprehensive understanding of what homeworking means for managers, we argue that it is necessary also to understand both the underappreciated past of the phenomenon as well as options for its projected future. A comparative – past, present, future – inquiry therefore portrays how a range of explicit (e.g. corporate restructuring, digital technology, government legislation) and implicit (e.g. responsible autonomy, cultural resistance, work–life balance) factors have influenced and affected the practice of managers working at home in recent times. Through content analysis, these factors are related to broader forces of strategic change, technological innovation and political regulation in describing the ‘contested terrain’ of modern managerial work. Amid a context of economic neoliberalism, work extensification and shifting spatio-temporal (home/work) boundaries, the paradoxical nature of homeworking – symptomatic of managers’ contemporary ‘struggle for a normal working day’ – is documented through a series of interview-based narrative investigations (conducted in 2002–2006, 2015–2019 and 2020–2021). Ultimately, the paper makes a case not only for greater historical retrospection, but also for deeper critical reflection, in studies of managerial homeworking, and notably when considering whether the practice will likely be extended, ended or otherwise in the coming decades.