The underrepresentation of males from particular equity groups in Australian universities continues despite recent gains in achievement. This article presents a case study of the transition of one Aboriginal student, Robbie, from a school located in the Western suburbs of Sydney to an urban Australian university. Drawing on recent theorisations of learner identities, we investigate the formation of Robbie's aspirations, as well as the support he is entitled to and capitalises upon. The case study captures how different aspects of Robbie's life interrelate, as well as how he accesses support over time in transitioning from secondary school to university. Exploring Robbie's journey as a learner compels us to think critically about equity programmes and emphasise the role of close family involvement, peer mentoring and personalised support to improve outcomes for students from underrepresented backgrounds.