The structural and material factors affecting the lived realities and prospects of tertiary success for South African students are complex and manifold. Inexorably, these lived realities impact the work of academic advisors who guide and support students throughout their higher education journeys. The purpose of this article is to contribute to the growing body of literature about academic advising in and for South African higher education contexts, and in particular the daily work of academic advisors in the country. This is achieved by first drawing on literature to elucidate the various structural and material constraints affecting the lives of many South African students, before reconciling what emerges from the literature with quantitative data collected by an academic advisor working at a South African university about his engagements with students over a three-year period. This phenomenological study is underpinned by social realist principles as proposed by Margaret Archer and draws in particular on the notion of structure to advance its argument. Additionally, the work of Boughey and McKenna on the decontextualized learner is incorporated to demonstrate why students in this country cannot be decontextualized from their lived realities. The article concludes by highlighting how the complex structural and material constraints that influence students' higher education experiences manifest in the day-to-day work of academic advisors. The authors propose that these insights be used to enhance responsiveness to student needs, while informing how the sector makes meaning of advising for the South African higher education context.