The purpose of this paper is to explore how socioeconomic and technological shifts in Canadian and American food production, processing, and distribution have impacted resilience in the food system. First, we use the social ecological systems literature to define food system resilience as a function of that system’s ability to absorb external shocks while maintaining core functions, such as food production and distribution. We then use the literature to argue that we can infer food system resilience by exploring three key dimensions: (1) the diversity of the food system’s components, (2) the degree to which the components are connected, and (3) the degree of decision-making autonomy within the food system. Next, we discuss the impacts of industrialization on these three factors within Canada and the USA. Specifically, we show how processes of corporate concentration, farm-scale intensification, mechanization, and the “cost-price squeeze” have led to a decrease in ecological and economic diversity, a high degree of spatial and organizational connectivity, and a diminished decision-making capacity for individual farmers. While this analysis is qualitative and heuristic, the evidence reviewed here leads us to postulate that our food system is becoming less resilient to external shocks such as climate change. We conclude by discussing four possible strategies to restore resilience and suggest a more transformational shift in food system politics and practice. Specifically, we argue that publicly led multifunctional policies may support more diversified production while programs to promote food system localization can increase farmer autonomy. However, these shifts will not be possible without social-structural corrections of current power imbalances in the food system. This policy discussion reinforces the value of the social ecological framework and, specifically, its capacity to produce an analysis that interweaves ecology, economy, and power.