The quality of student learning depends largely on how well we design our curriculum and the pedagogies we use within this curriculum. A successful Flipped Classroom (FC) is no exception: to engage students and ensure learning requires carefully considered design and implementation. This chapter teases out, and more closely examines, the key critical success factors from the perspective of the changes that are required in both student and facilitator expectations and roles. In addition, a model for designing a FC provides a structured approach that emphasises a ‘context-first’ strategy.