Academic freedom is often regarded as an absolute value of higher education institutions. Traditionally, its value is related to such topics as tenure, and the need for academic work to be free from undue political influence and other pressures that can challenge time-consuming research processes. However, when an analysis of student freedom begins with arguments about free research and free speech, undergirded as they generally are by liberal political philosophy, other considerations, related to broader views of freedom, can slip through the cracks. In this essay, I want to take a step back from typical discussions of academic freedom, to take a broader perspective, before considering how freedom relates to student experience. The first part of this essay explores diverse elaborations and defences of freedom: How it is upheld in the liberal philosophy of Kant, the critical pedagogy of Freire, existentialism, and the capabilities approach to development. Exploring the often contrasting insights and implications of these views, I then connect relevant theoretical understandings derived from them to an exploration of the experience of freedom and (lack thereof) of students (in a university context). This essay thus considers how student freedom, and student academic freedom, are more precarious concepts than typically assumed.