The underrepresentation of boys from Aboriginal and Torres Strait Islander peoples in Australian universities continues despite recent gains in widening participation. This article presents a case study documenting the transition of one Indigenous student, Robbie, from an underprivileged school located in the Western suburbs of Sydney to an urban Australian university. We focus first on his experience at university before considering how an opportunity with Work-Integrated Learning (WIL) influenced his confidence and motivation. Central to the analysis is the continual and contentious nature of Robbie's identity work concerning the opportunities he encounters. In exploring Robbie's journey as a learner, his experiences compel us to reflect on how facets of his learner identity change in relation to opportunities and what this may mean for how equity programmes provide support for vulnerable learners -- specifically how we can improve outcomes for young men from underrepresented backgrounds.