Professionals are increasingly involved in attempts to under- stand and address problems with wicked tendencies, which require crossing boundaries between disciplines, organisa- tions and stakeholder perspectives. This multiple-case study investigated six higher professional education courses in order to develop better understanding of how teachers fos- ter the development of students’ boundary-crossing exper- tise through enhancing relevant learning processes in courses focussing on wicked-problem-solving in interdisci- plinary 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 pro- cesses. Data came from semi-structured interviews with tea- chers, 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 stu- dents experience at boundaries when navigating complexity, uncertainty and value divergence was identified as an impor- tant element of these enabling strategies.