This paper presents a case study where twelve graduate students undertook the demanding role of the adaptive e-course developer and worked collaboratively on an authentic and complex design task in the context of open and distance tertiary education. The students had to work in groups in order to conceptualise and design a learning scenario for adaptive learning, develop learning materials and adaptive learning strategies, implement the respective adaptive e-course and finally, reflect on their experience. The primary goal of this intervention was to engage the students in the whole lifecycle of a Technology Enhanced Learning design artefact. In teaching highly complex skills for the ill-structured domain of Learning Design the four components instructional model (4C/ID) was exploited. Students were exposed to a wide range of interconnected issues and made design choices. Mixed research methods are used to conclude on the effectiveness of the intervention. Implications of this study include design guidelines towards an environment that implements complex adaptive behaviour in today's learner-generated digital world where Computer Supported Collaborative Learning often converges with Computer Supported Collaborative Design.