The central concern of the thesis is to problematise the complexity of the relationship between student learning and the teaching-learning environment in medicine as experienced by students. The thesis argues that learning material presented to students offers only potential for learning. What students make of that potential is influenced by a number of different variables and as such this needs to be investigated empirically. High-quality learning is an important goal for all higher education and previous research together with the empirical findings presented in this thesis convey the importance for students to seek a holistic approach to learning. Such a learning approach encompasses not only learning of facts and theories but also includes exercising an ability to reflect and reason, to organise facts and theories into wholes, and to explore how they relate to each other. Most importantly, it involves the ability to understand the grounds on which facts and theories are chosen for specific purposes depending on context. The thesis explores these issues by drawing on findings from three studies of medical students’ experiences of learning and understanding and how students’ personal understandings of subject content in medicine come to the fore in their work on learning tasks. By applying a context-oriented methodological perspective on learning, focusing on what students actually do in a learning situation, the thesis enables an in-depth investigation of relationships between aspects of content, context and the individual. The results show that the learning environment in the medical programme to a large extent does not make sufficient room for students to express understanding of this dynamic character. In the thesis it is argued that to facilitate such an understanding it is necessary for both students and teachers to increase awareness of the context-dependency of subject content, facts and theories, and the different meanings content takes depending on context of use.