Nelson and Nelson (1987) coined the term "intertwingularity" to express the complexity of interrelations between the various facets of human knowledge. This theoretical paper explores the intertwingularity of learning environments by proposing a model for understanding and operationalising the relationship between learning environments and their relative degrees of cooperative freedoms and the learning technologies used by teachers and students. Two case studies demonstrate that these types of learning environments generate far more complexity, in the form of recursion and iteration, than do traditional learning environments. While these types of distributed learning networks have been observed in adult learning settings, they have only been rarely observed in K-12 classrooms. Implications for teacher education and teacher education research are discussed.