Recent advancements in breeding perennial rice and the perennial grain Kernza® illustrate progress in converting an agroecology moonshot into a deeply rooted reality. In this chapter we highlight research efforts underway to advance the scientific and sociocultural development of new perennial grain crops and cropping systems. Sections describe concentric circles of targeted research that begins with plant breeding, and expands into ecological intensification of cropping systems, supply chain development, farmer adoption, food science, and community learning. Together these elements contribute to a working model of perennialization that may be adaptable to a wide range of cultural geographies around the world.