This study examines gaps between work as imagined under labor regulations and as performed in the digital age. Through interviews, content analysis of corporate documents and case studies of enterprise software applications, it explores the competing views of spatial, temporal and data boundaries of digital work held by labor stakeholders—employers, workers, retailers and advertisers—in the absence of labor regulations adapted for the digital age. Driven by the desire to increase productivity, protect corporate assets and monitor workers, employers establish corporate policies that embrace the benefits of fluid work and non-work boundaries without taking on associated responsibilities for worker protection. Workers on the other hand are influenced by their socio-economic circumstances and engage in boundary management behaviors that undermine their interests or preferences. In pursuit of profit maximization, enterprise software companies, retailers and advertisers amplify an already dominant employer perspective, leaving workers at a heightened risk of the adverse effects of blurred work boundaries—including lost wages, personal time and privacy.