Research studies of post-school education and training conducted in Australia and internationally have revealed a mosaic of students' education and employment experiences, with a multiplicity of nonlinear pathways. These tend to be more fragmentary for disadvantaged students, especially those of low socio-economic background, rural students, and mature aged students seeking a "second chance" education. Challenges faced by students in their transitions to higher education are made more complex because of the intersection of vertical stratification created by institutional and sectoral status hierarchies and segmentation, especially relating to "academic" and "vocational" education and training, and the horizontal stratification of regional, rural and remote locations in which students live. If we are to achieve the equity goals set by the Bradley Review (Bradley et al., "Review of Australian Higher Education Final Report," 2008) we need to acknowledge and work with the complex realities of disadvantaged students' situations, starting at the school level. Interrelated factors at the individual, community and institutional level which continue to inhibit student take-up of higher education places are discussed in the context of discursive constructions of "disadvantage" and "choice" in late modernity. Research highlights the need to facilitate students' post-school transitions by developing student resilience, institutional responsiveness and policy reflexivity through transformative education.