Professionals are increasingly involved in attempts to understand and address problems with wicked tendencies, which require crossing boundaries between disciplines, organisations and stakeholder perspectives. This multiple-case study investigated six higher professional education courses in order to develop better understanding of how teachers foster the development of students' boundary-crossing expertise through enhancing relevant learning processes in courses focusing on wicked-problem-solving in interdisciplinary and multi-stakeholder contexts. We viewed students' relevant learning processes as learning mechanisms that foster boundary awareness (identification and reflection) and boundary work (coordination and transformation) and considered teachers to be enablers of such learning processes. Data came from semi-structured interviews with teachers, students and stakeholders, observations and document study. We identified nine interrelated enabling strategies teachers used. To foster students' observation of wickedness through boundary awareness, they encouraged mutual acquaintance, open exploration, opportunities for learning, and multi-perspectivity. To foster students' action through boundary work, they encouraged initial contact, joint action and multifaceted perspectives on value creation. To foster the interplay between boundary awareness and work, they encouraged successive refinement and structure while embracing wickedness. Balancing the tension that students experience at boundaries when navigating complexity, uncertainty and value divergence was identified as an important element of these enabling strategies.