In competency-based medical education (CBME), which is being embraced globally, the patient-learner-educator encounter occurs in a highly complex context which contributes to a wide range of assessment outcomes. Current and historical barriers to considering context in assessment include the existing post-positivist epistemological stance that values objectivity and validity evidence over the variability introduced by context. This is most evident in standardized testing. While always critical to medical education the impact of context on assessment is becoming more pronounced as many aspects of training diversify. This diversity includes an expanding interest beyond individual trainee competence to include the interdependency and collective nature of clinical competence and the growing awareness that medical education needs to be co-produced among a wider group of stakeholders. In this Eye Opener, we wish to consider: 1) How might we best account for the influence of context in the clinical competence assessment of individuals in medical education? and by doing so, 2) How could we usher in the next era of assessment that improves our ability to meet the dynamic needs of society and all its stakeholders? The purpose of this Eye Opener is thus two-fold. First, we conceptualize – from a variety of viewpoints, how we might address context in assessment of competence at the level of the individual learner. Second, we present recommendations that address how to approach implementation of a more contextualized competence assessment.