Towards the end of the past decade, signs were emerging as to future challenges associated with impending intersections between the ageing of global rural populations and their impacts on agricultural production and food safety. In a landmark paper for the Food and Agriculture Organisation (FAO), Iaquinta et al. (1999) made a strong plea for additional research in the field and developed a schematic highlighting the linkages between ageing, land tenure, intergenerational change and agricultural production for developing countries. The link to sustainability within this schematic was implied rather than highlighted and the importance of the issue for the developed world was glossed over. This chapter argues that this is a vital challenge for Australia now at the end of the first decade of the twenty-first century, as the country ages and the transition of knowledge from the 'baby boom' generation impacts at all levels of Australian society. It draws on continuing research being undertaken in Western Australia as part of an international research group focusing on sustainability and conservation. It takes up the schematic as designed by Iaquinta et al. and highlights the key issues for land tenure, the impact on rural values, natural resource management and future sustainability with specific focus on the south coast region of the state.