Finding solutions for complex societal problems requires cross-boundary collaboration between multiple stakeholders who represent various practices, disciplines and perspectives. The authentic, multi-stakeholder Regional Learning Environment (RLE) is expected to develop higher education students’ capabilities for working in multi-stakeholder settings. However, the effectiveness of the RLE, including its typical cross-boundary learning environment characteristics, has not been investigated. This thesis shows that the RLE develops students’ domain specific expertise and various generic competencies. The learning environment characteristics of working in multi-disciplinary student groups, working highly intensive with stakeholders, and a high coaching intensity strengthen competence development. Explicit workshop-based support of students’ boundary crossing working and learning stimulates the amount of student-stakeholder collaborative activities, and activates students’ boundary crossing learning. Teachers fulfil new out-of-school oriented roles and tasks in the RLE and should master new boundary crossing competencies. Existing higher education teacher profiles are recommended to be adapted to become out-of-school proof.