This essay inquires whether digitally transformed work can be virtuous and under what conditions. It eschews technological determinism in both utopian and dystopian versions, opting for the premise of free human agency. This work is distinctive in adopting an actor-centric and explicitly ethical analysis based on neo-Aristotelian, Catholic social teaching (CST), and MacIntyrean teachings on the virtues. Beginning with an analysis of digital disruption, it identifies the most salient human advantages vis-à-vis technology in digitally transformed work and provides philosophical anthropological explanations for each. It also looks into external, organizational characteristics on both the macro and the micro levels of digitally transformed work, underscoring their ambivalence (efficiency and profits vs. exclusion and exploitation, flexibility and freedom vs. standardization and dependency) and the need to mitigate their polarizing effects for the sake of shared flourishing. The article presents standards for virtuous work according to neo-Aristotelian, CST, and MacIntyrean frames and applies them to digitally transformed work, giving rise to five fundamental principles. These basic guidelines indicate, on one hand, actions to be avoided and, on the other, actions to be pursued, together with their rationales.