Despite the economic, environmental and patient-related imperatives to prepare medical students to become health promoting doctors, health promotion remains relatively deprioritised in medical curricula. This paper uses an in-depth case study of a health promotion curriculum implementation at a large UK medical school to provide insights into the experiences of teachers and learners across a range of topics, pedagogies, and teaching & assessment modalities. Topics included smoking cessation, behavioural change approaches to obesity, exercise prescribing, social prescribing, maternal and child health, public and global health; with pedagogies ranging from e-learning to practice-based project work. Qualitative methods including focus groups, analysis of reflective learning submissions, and evaluation data are used to illuminate motivations, frustrations, practicalities, successes and limiting factors. Over this three year implementation, a range of challenges have been highlighted including: how adequately to prepare and support clinical teachers; the need to establish relevance and importance to strategic learners; the need for experiential learning in clinical environments to support classroom-based activities; and the need to rebalance competing aspects of the curriculum. Conclusions are drawn about heterogeneous deep learning over standardised surface learning, and the impacts, both positive and negative, of different assessment modalities on these types of learning.