In the Australian context, high school careers education has received very little close-focused attention, particularly on its integration into curriculum and teacher's time, and how students experience it, in both vocational and more academic streams. This presentation explores these aspects of career education using qualitative data from two studies: (1) The Aspirations Longitudinal Study; and, (2) The Pathways the Medicine Study. Both studies focused on exploring post-school education and career aspirations of high school students in regional and rural New South Wales. The paper draws upon data from the Aspirations Longitudinal Study, specifically from focus groups conducted with 77 students aged 12-18 years from a rural town. It also draws on focus group data from 33 academically-able students aged 14-16 years from a regional city who took part in the Pathways Study on aspiration to medical school. An analysis of focus group data revealed the following themes: differences in experiences of career education related to vocational and academic streams; difficulties related to accessing work experience and 'hot' knowledge for students interested in high status professions; and the perceived limited capability of school career advisors in assisting students in practical and aspirational exploration of the world of work. The paper concludes by highlighting specific aspects of the conundrum of career education as it plays out high schools, and suggests ways in which it might be reconfigured to better benefit young people, particularly those experiencing socio-economic disadvantage in rural and regional Australia.