Uncertainty is a feature of healthcare practice. In recognition of this, multiple health profession governing bodies identify uncertainty tolerance as a healthcare graduate attribute and evaluate uncertainty tolerance within new graduate cohorts. While it is clear that uncertainty tolerance development for healthcare learners is valued, gaps remain for practically addressing this within healthcare curricula. Guiding frameworks for practical approaches supporting uncertainty tolerance development in healthcare learners remains sparse, particularly outside of medicine and in certain geographical locations. As uncertainty tolerance is increasingly recognised as being, at least in part, state-based (e.g. contextually changeable)– a broader understanding of teaching practices supporting uncertainty tolerance development in diverse health professions is warranted. This study explored educators’ teaching practices for purposefully stimulating learners’ uncertainty tolerance. Semi-structured interviews investigated how academics at a single institution, from diverse fields and health professions, stimulate uncertainty across multiple learning contexts. Framework analysis identified three themes for stimulating uncertainty: Purposeful questioning, Forecasting uncertainty, and Placing learners in unfamiliar environments, with characterisation of these themes (and related subthemes) also described. Many of the identified themes align with aspects of existing learning theories suggesting that curricular frameworks supporting learner uncertainty tolerance development may be informed by theories beyond the boundaries of health professions education research.