Surgery simulation is a core application area of computer haptics and simulation technologies, giving aspiring surgeons theopportunity to practice hands-on using complex manual actions before encountering real patients. The design of the haptic feedback isan important aspect of developing such tools, but the design of a surgery simulator involves also many other aspects. This paperpresents a long-term case of designing and iteratively developing an oral surgery simulator named Kobra. Based on feedback fromsurgeons, students and curriculum developers, as well as through insights from actual design work, particular aspects of the designthat support learning have been identified and articulated. Based on experience of designing simulator exercises originating fromauthentic patient cases it is shown how simulation techniques can be appropriated to support oral surgery teaching, through targetedinteraction design. The study highlights important aspects to consider for further design work in this domain, i.e. the value of realismand surgical relevance, the social setting of teaching surgery, content authenticity, and the physical qualities of the simulator.