Context matters in the practice of interpreting but too often the complexities and implications of context are not adequately defined in interpreter training. Instead, learning about the many and varied contexts that interpreters are called into is left to on-the-job experience. Over the last twenty years, Robyn Dean and Robert Pollard have offered practitioners, educators, and trainers ways to identify and talk about the interpreting context and how to more effectively prepare interpreters for working in those contexts. Much of that work has been devoted to the contexts of medical and mental health. This presentation explains how medical interpreting educators can help to not only define context but teach it and assess practitioners’ ability to understand and apply it in professional practice. As medical education has worked to improve the clinical skills of providers so too should medical interpreter education. This can happen by bringing interpreter practitioners incrementally closer to the medical contexts, that is to improve and assess their clinical skills.