The paper discusses qualitative findings from an in-depth study of the school choices of 65 parents living in rural and remote areas of Tasmania and their views about the need for their children to move out of the area to pursue education at secondary and post-secondary level. A constructivist analysis of open-ended survey questions and focus group discussions formed part of a broader mixed-methods approach and probed the affective 'subtext' of instrumental survey responses. Findings contribute to our understanding of the interaction of affective, instrumental and structural factors influencing rural parents' educational decision-making in the neo-liberal policy context, especially with regard to decisions perceived by parents as 'risky' with respect to their own future employment and financial expectations. External threats to rural livelihoods, such as economic downturns and natural disasters create parents' feelings of anxiety about children's educational futures and are experienced differently by those living on farming properties or in small rural towns. Parents' perceptions of local and urban school availability, access and quality differ by locality and region. Educational outcomes reflect multidimensional structural, socio-economic and cultural constraints shaping school choice. Membership of voluntary associations, which provides supportive informational networks and develops shared social capital, appears to help parents to overcome socio-economic inequalities and improve their children's prospects of educational success. The interplay of social class, gender and place attachment is examined with reference to Bourdieu's concepts of habitus and disposition, as well as the processes by which parents try to transmit intergenerational advantage through educational choices.