Emerging Artificial Intelligence-enhanced technology platforms in education warrant attention to exploring new learning strategies and dynamics. Keeping up with the accelerating momentum to bring classic traditional learning activities to Artificial Intelligence-supported platforms may unbalance the interest in developing the participants' higher-order thinking. This article presents case study research of an Artificial Intelligence-based technological platform to measure complex thinking traits of higher education participants in an Ideathon learning scenario. The didactical strategy was grounded in the Transition Design approach, with Sharing Economy as the challenge. An overview of the process for developing Artificial Intelligence-supported activities, the challenges and risks identified in the development, and a classification model and enhancements for future implementation in a subsequent pilot are presented. The findings set a guideline for balancing Artificial Intelligence-powered educational activities and the development of the participants' complex thinking.