System Dynamics (SD) is an experimental, quantitative approach for designing structures of social systems and policies that are compatible with a social system’s growth and stability objectives. The experimental model approach for the design of large scale systems is the key for learning about human organizations. Before elaborating on the types of learning environments that can be designed on the basis of SD models, this article presents a social systems theory, distinguishing classical and autopoietic systems theory. Two generic models are presented, which reflect both theoretical points of view and constitute different types of learning environments. The author summarizes epistemological views on learning and growth of knowledge in the context of learning as acquisition and learning as interaction. Subsequently, by building on the actor approach of social systems, learners are embedded in learning environments. They should learn to deal with the duality of structure of social systems, that is, learn to produce and self-reproduce structures as a context for action. Finally, these views are linked to three simulation modes and to participative design of learning environments.