In highly marketised higher education systems, massification has afforded greater access, particularly for first-in-generation students. Generally, this expansion has been fuelled by neoliberal ideologies that valorise the notion of choice and promise of social mobility. In this study, using interviews with 25 first-generation students, the issue of choice is critically examined in one of the earliest arenas of neoliberal experimentation: the Chilean higher education system. The study found that these first-in-generation students encountered complex and multi-levelled challenges in making higher education choices. Such choices were firmly anchored in differing levels of aspiration, and were strongly mediated by both family and school social capital. As a result, we propose an addition to traditional conceptions of choice: students (and their families) who act as strategic choosers. This outcome challenges the notion that first-in-generation students encounter unitary trajectories or equitable choices in encountering higher education.