This paper reports on the views of key members of the educational community about student engagement and retention in rural, regional and disadvantaged areas of the Australian state of Tasmania. It provides insights into the attributed reasons for the longstanding low levels of student retention in Tasmania, and the possible ways to militate against the widely censured problem of students leaving school too soon. The paper draws from principles of Bronfenbrenner's model of ecology to situate the 25 participants who formed the sample of the study in the "exosystem" of the environment of the young people whose educational attainment and retention in schools is the focus of this work. Data analysis generated three major themes: "families and the socio-cultural environment"; "teachers and teaching"; and "the school system." The study's findings play an important role in prompting us to question when, and if, the dire situation of student dropout in the state and in similar contexts worldwide will begin to be reversed. Implications of the work include the need to develop and sustain a strong policy environment in which high-quality education and schooling success are contextualised as key features to which members across the systems and sections of society can contribute.