This paper explores the relations between agricultural modernization and sustainable agriculture. The point of departure is the observable decrease in the sustainability and social–ecological resilience of agricultural and food systems. We ask where, precisely, the notions of agricultural modernization and agricultural sustainability contradict each other. In more concrete terms we ask what forms of modernization makes agriculture more (or less) sustainable. Our literature review shows that while the term ‘sustainable agriculture’, has been extensively debated, the term ‘agricultural modernization’, while carrying a positive and forward-looking connotation, remains poorly defined. To address this gap, we draw on evidence from real-life cases in fourteen countries in an attempt to interpret how the two concepts are perceived in very different contexts. These case studies show that different understandings of modern and sustainable agriculture coexist and that agricultural development follows diverse pathways. We conclude that the growing demands for an agricultural and food system that is more resilient, equitable and inclusive can be met by providing more support for the many divergent trajectories of agricultural modernization that practitioners are actually pursuing: trajectories that are often more attuned to the imperatives of ecology and to changing socio–economic preferences than the classical modernization trajectory.