There has been considerable discussion about retention of students in education beyond Year 10 in Tasmania reflective of the fact that the state has the lowest retention rates for young people continuing in some type of formal education or training beyond Year 10 in Australia. Importantly, the challenges for Tasmania are shared by other educational jurisdictions nationally and internationally, particularly those that share similar economic and demographic characteristics (Lamb et al., 2015). This article reports on a series of in-depth case studies as one aspect of a three-year Australian Research Council Linkage project undertaken in collaboration with the Tasmanian Department of Education (DoE) examining issues associated with retention, especially for students in rural, regional, and disadvantaged areas. Three inter-related themes (viz. sociocultural; structural; curriculum, teaching and learning) are identified that seem collectively and interdependently to play key roles in determining whether many young people continue their education beyond Year 10. The three themes are conceptualised and discussed as a wicked problem: a highly complex educational, social and cultural problem, involving issues that require 'thinking that is capable of grasping the big picture, including the full range of causal factors underlying them' (Australian Public Service Commission (APSC), 2007, p. iii). The research suggests that the challenges to effecting positive changes in retention rates in the future are highly complex. Structural solutions alone are not sufficient. Responses, at leadership, policy and practice levels, will also need to address curriculum issues as well as deeply held cultural views and practices evident across various sectors of society, including families, communities and educators themselves.