Background: During clinical clerkships students experience complex and challenging clinical situations related to problems beyond the domain of the "Medical Expert". Workplace routine may leave little opportunity to reflect on these situations. The University of Zurich introduced a mandatory course directly after the clinical clerkship year (CCY) to work up these situations. Prior to the course each student submitted a vignette on a case he or she had perceived challenging during the CCY and which was not related to the domain of the "Medical Expert" role. In this paper we want to characterize these cases in respect to most prominent themes and related CanMEDS roles. The goal was to inform clinical supervisors about potential teaching demands during the CCY. Methods: All case vignettes submitted by a years' cohort were analysed by three researchers in two ways: for the clinical characteristics and the main theme of the underlying problem and the most prominent CanMEDS roles involved. Themes of the underlying problem were aggregated to overarching topics and subsequently to main categories by pragmatic thematic analysis. Results: 254 case vignettes covered the whole spectrum of clinical disciplines. A wide range of underlying themes could be assigned to five main categories: "communication within team" (23.2%), "communication with patients and relatives" (24.8%), "patient behavior and attitudes" (18.5%), "clinical decision making" (24.0%), and "social and legal issues" (9.4%). Most frequent CanMEDS roles were "Communicator" (26.9%) and "Professional" (23.5%). Conclusions: Cases students perceived as challenging beyond the "Medical Expert" were reported from all clinical disciplines. These were mainly related to communicational and professional issues, mirrored by the CanMEDS roles "Communicator" and "Professional". Therefore, supervisors in clinical clerkships should put an additional teaching focus on communication and professionalism.