This chapter describes the development and consequences of agricultural intensification and explains key forces that sustain industrial agriculture, despite its many, well-documented harms. We then define transition and transformation toward agroecology, drawing on conceptual frameworks from systems thinking and the social sciences. We argue that combining the ecological and social science dimensions of agroecology is central to advancing transitions and scaling them to larger food systems, especially drawing on insights from the perspective of political ecology. Political ecology seeks to understand underlying power dynamics, and values, goals, and beliefs of actors in a system, which is essential for influencing the strongest leverage points for transformative change. As long as institutions and power relations reinforce industrial agriculture through policies, subsidies, and markets while penalizing agroecological practices, most industrial farmers will not risk transitioning away from the dominant regime. Three case studies illustrate distinct pathways for agroecological transition.