This study investigated the influence of the teacher and family relationships during secondary school for 18 to 22 year old students who had dropped out of secondary school and were attempting to gain access to tertiary study through a tertiary bridging program at a regional university. 144 students from two student cohorts completed a questionnaire intended to facilitate an understanding of how social context influenced secondary school attrition. It was identified that students who had not completed secondary school reported significantly lower levels of emotional engagement with school and poorer relationships with teachers. The study concluded that the residential situation and the quality of student-teacher relationships influenced the quality of the academic outcomes achieved in secondary school, with the student-teacher relationship being the dominant factor. It was also concluded that, while secondary school completion was significantly lower for students who did not reside with both parents, the family situation was not predictive of school completion. Rather, it is hypothesised that the wider contextual problems associated with family dysfunction which manifest in a poor school experience were the cause of the failure to complete secondary school. The implications for secondary school and tertiary bridging educators are discussed. At a time of increased emphasis on young people gaining accreditation and qualifications for entry into work (Bentley & Gurumurthy, 1999), the problem of students dropping out of study programs has engaged researchers (e.g. Cairns, Cairns, & Neckeman, 1989; Janosz, LeBlanc, Boulerice, & Teremblay, 1997; Jimerson, Egeland, Sroufe, & Carlson, 2000; Rumberger & Larson, 1998). At the macro-level, governments are increasingly concerned with the stock of human capital in the economy (Kennedy & Lee, 2008) while at lower levels communities are concerned with the impacts of under-qualified young people. In 2008 a report commissioned by the Australian government (Bradley, Noonan, Nugent, & Scales, 2008) nominated a target for the Australian tertiary education sector of 40% of 25to 34 year old Australians to possess at least a bachelor level qualification by the year 2020. At the time the report was produced only 29% of the target group was possessed of such a qualification. Australian Journal of Teacher Education Vol 36, 9, September 2011 23 The study reported below is in part a re-visitation of the topic of high school drop-outs, but from a different perspective. It seeks to add to the literature explaining the reasons for students dropping out of high school, but from the perspective of a student cohort who have made a decision to return to study, in this case by applying for entry to university through a special preparatory course. Opportunities to collect a group of high school drop-outs for research purposes are rare, and therefore valuable. The findings can be propitious, in that they help to understand why students drop out of school and suggest, importantly, what conditions need to be in place in tertiary preparation programs to prevent a recurrence of the phenomenon, and a positive educational outcome for these young people who are re-committing to education.