Future clinicians are increasingly going to be challenged with relatively atypical cases and complex situations, that demand expert judgement and innovative solutions. Adaptive expertise has been described as the capacity to modify approaches to solve problems creatively, enabling individuals to thrive in a changing environment. This paper presents how research on “adaptive expertise” can inform pharmacology teaching in medical curricula, placing emphasis on training clinicians who are adaptive prescribers. Pharmacology and drug-related information when contextualised with the clinical picture facilitate formation of necessary connections, which can potentially assist in retrieval of knowledge in future situations. The organization and coordination of the knowledge appears more important than the quantity for expert performance. Learning activities and assessments should not only stimulate learners to explore the topic, but also encourage errors, as this allows individuals to try out alternative methods and gain a better understanding of the subject. Metacognition and self-regulated learning can aid adaptability, as experts consciously strive to keep knowledge active and fluid rather than automated. The paper recommends pragmatic strategies applicable at the broader course level as well as the individual sessions, which are a reorientation to already existing tools to reinforce cognitive integration, productive struggle and formative support.