Flexible learning is now well entrenched in the policy, curriculum, and course delivery frameworks of many higher education sectors in the Western world. However, because of the ambiguous nature of the terms, teachers are often faced with ill-defined expectations from their institution to ‘be flexible’—to make choices about where, when, and how they will offer the various elements of their curriculum. The negotiable meanings of flexibility cluster around the divergent perspectives of a range of stakeholders, including pedagogists, managers, and technologists. Teachers are often unsure of the motives behind the push towards flexible learning: Are they being asked to save money by putting their courses online and reducing their face to face teaching? Are they being asked to better meet the needs of 21st century students and therefore increase enrolments? Is it about improving student learning by refocusing on student-centred learning and lifelong learning? Is it about harnessing the educational potential of new technologies? Tucked within this confusing area of higher education sits flexible assessment—a relatively neglected theme in the flexible learning story.