Medical education's mission includes ensuring that students possess a working fund of knowledge and the skills needed to apply this knowledge appropriately to clinical situations.  Assessments can motivate students to learn and evaluate whether they have gained the breadth and depth of knowledge required for practice.    Traditionally, assessment of knowledge has relied heavily on multiple-choice questions (MCQs). Advantages of MCQ-based assessments include reliability and validity; however, by their nature MCQs may limit preparation for care of patients who do not present with choices. The challenge for medical educators is to assess deep learning through problem-solving and application of knowledge to solve a variety of clinical and scientific problems through divergent, rather than convergent, thinking. A key advantage to open-ended questions (OEQs) is that they enable students to describe their reasoning, thereby demonstrating their ability to explain the application of basic science principles to clinical problems.  The purpose of this session is to engage the medical education community in a conversation about the possibilities of using OEQs to promote the learning.