Cases, presenting apparently real life situations, can be used to prompt students to integrate theoretical knowledge from across a number of subject areas and to develop analytical skills, and as such, act as a starting point for learner-centered authentic learning opportunities. Cases can also be used as a basis for written or skills-based assessments, the focus of this article. An extensive review of the health profession literature has not revealed evidence-based guidelines to the process of assigning case difficulty. We have evaluated a model from business education, the Case Difficulty Cube, which proposes assignment of case difficulty based on three dimensions—analytical, conceptual, and presentation—and adapted this model for consideration in health education. The development of the model was influenced by reflections of individual academics’ experiences with the use of cases in written assessments. This article proposes a model for evaluating case difficulty in pharmacy education.