Background: It is widely recognised internationally that participation in higher education is likely to lead to increased opportunities and resources. However, only a minority of learners from Roma backgrounds continue into post-compulsory education. As important research into inclusion continues, more attention must be paid to the identification of practices that can help break down barriers and support the participation of Roma students in post-compulsory education. Purpose: The research sought to gain insight into particular factors influencing the decision-making processes of three students from Roma backgrounds who chose to pursue an academic pathway. Method: The setting for this qualitative study was a school in Spain located in a socioeconomically disadvantaged and predominantly Roma neighbourhood whose students had never previously participated in pre-university studies (courses preparing students for university entrance). In-depth interviews were conducted with three Roma students in their last year of compulsory education who were about to move on to pre-university studies, as well as with three significant adults: a Roma mother, a Roma role model working at the school, and the school principal. Findings: The analysis of participants' narratives suggested that, according to their views, the implementation of a set of successful educational actions involving high expectations, the involvement of Roma families, the influence of positive Roma role models and engagement with dialogic interactions contributed to the continuation of these three Roma students on a trajectory towards post-compulsory education. Conclusions: The study highlights some noteworthy factors that can be involved in transforming a context from one where access to university is not considered to be an option and towards a new one in which university becomes a real choice.