This chapter considers the potentially ‘uncomfortable spaces’ involved in the pedagogies and practices of online enabling education programs. These programs present distinct philosophical ambiguities, situated as they are between the seemingly oppositional rhetorical discourses of, on the one hand, widening participation – where online platforms provide access to higher education for those who may be otherwise excluded from educational opportunity – and, on the other, online education conceptualised as part of the neoliberal educational agenda – where ‘online’ equates to institutional efficiencies such as cost reductions and increased ‘footprints’. To illuminate these complex ambiguities and discomforts, we bring together literature regarding the neoliberal promises of online education with the realities and perceptions of online enabling students. While online enabling students internalise neoliberal discourses in terms of their employment goals and academic achievements, their experiences and attitudes render these discourses complex by layering them with notions of family beneficence, community belonging, self-identity, and self-worth. We argue, then, that while neoliberalism and widening participation are not mutually exclusive discourses, online enabling programs, and the higher education institutions that host them, should privilege their founding philosophies, whereby engagement in education can result in a diversity of outcomes which defy easy neoliberal classifications and serve the wider public good.