This chapter takes a closer look at the situation of underprivileged students in their post-secondary education (PSE) choices upon graduation from secondary education. After reviewing the attainment gap from the literature, this chapter focuses on students' perspectives on pursuing PSE, including their awareness of choices, confidence in accessing the PSE institutions, impacts of significant others, and self-agency in navigating the process of certainty, uncertainty, and discontinuity. The interview data reveal that these students are aware of the challenges ahead within the intersectionality of multiple disadvantageous contexts. Although future aspirations may be beyond their reach nevertheless, they demonstrate a degree of agency. Their perspectives and reflections on success and future aspirations, struggles, and obstacles are unveiled, and the support available from families, schools, and their self-agency are discussed.