This chapter invites readers to think in a new way about sustainability. The chapter works from a “regenerative” food systems framework which recognizes that fundamental reform to food production is needed to break from the status quo in order to deliver food system health and justice. The chapter first summarizes proponents’ claims that big data and sophisticated computing for analyzing them will drive a sustainability revolution in food production (and practices along the entire food chain). It then draws on qualitative interviews and digital ethnography to argue that the current trajectory for digital agriculture is one which supports the continuation of large-scale, low-value crop farming amended for more judicious use of chemicals and water. Therefore, digital agricultural tools are not regenerative but rather, at least in their current economic and legal infrastructures, they are reproducing a number of social and cultural food system challenges.