In response to the increasing pressure on agri-food systems to reconcile productivity, environmental sustainability, and climate resilience, regenerative agriculture (RA) has emerged as a potential long-term strategy for systemic transformation. At the same time, the diffusion of Industry 4.0 (I4.0) technologies is reshaping agricultural practices. In fact, digital tools are increasingly being integrated into farming processes to improve efficiency, data management, and supply chain transparency. Yet, despite the simultaneous expansion of these two parallel trends, the extent to which digital technologies can concretely support regenerative practices remains underexplored. This thesis addresses this gap by comparing high-tech, technology-intensive configurations with predominantly nature-based approaches.