Current approaches to understanding learning imply that authentic learning experiences assist students to develop appropriate and effective understandings. Authentic learning experiences are those that are personally relevant from the learner’s perspective and situated within appropriate social contexts. In planning for authentic learning to occur, tensions can emerge between providing real world "natural" experiences and the nature of experiences that are possible to offer within institutions, which can often be "artificial or staged", and seen as inauthentic by students. Bridging the gap between the learning taking place within formal institutions and learning within real life communities of practice can be difficult for university teachers. This paper reports the efforts of a university teacher who, through a one-semester course, endeavoured to bridge this gap between university study and learning about the world of business management. Data sources included the teacher’s plans, diary and written reflections on his activities related to his teaching during the semester; course materials; teacher and student interviews; and classroom observations undertaken by the researchers. The various strategies the teacher used to develop authenticity in students’ learning experiences are discussed, as well as the teachers’ reflections on how he tried to capitalise on the formal structures possible in a university setting to support his students as they developed their understandings about what it is like to be practicing members of the business management community. Implications for teaching and learning in general, and for university staff development, are outlined.