There is a growing demand to enhance entrepreneurship. This study aims at producing knowledge that can assist teachers in designing and supporting collaborative learning of entrepreneurship in vocational education. A qualitative case study approach was adopted. The outcome of this study provides a better understanding of the factors that hinder and enable collaboration, as related to entrepreneurship education in initial vocational education and training. In practice, nine dimensions of descriptive factors that hindered the exercise and nine distinct descriptive factors that acted as enablers were identified. This study suggests that, although the script of the learning task creates the setting for collaborative learning, the positive style of working together seals the successfulness of the exercise. Moreover, designing the complexity of the computer-supported collaborative learning task seems to be a challenging process that balances between being simple enough and yet offering sufficient complexity. Finally, the findings illuminate the teacher's support as a valuable part of the collaborative learning process.