Flexible approaches to online learning are gaining renewed interest in some part due to their capacity to address emergent opportunities and concerns facing higher education. Importantly, flexible approaches to online learning are purported to be democratizing and liberatory, broadening access to higher education and enabling learners to participate in educational endeavours at "anytime" from "anyplace." In this paper, we critique such narratives by showing that flexibility is neither universal nor neutral. Using critical theory, we demonstrate how flexibility assumes imagined autonomous learners that are self-reliant and individualistic. Through relevant examples, we show how such a framing to flexibility is oppressive, and argue that a contextual, relative and relational understanding of flexibility may in fact be more liberatory. Such an approach to flexibility, for example, may involve contextual and relational efforts to relax prescribed curricula within courses or programmes of study.