This paper analyses a community-based educational program involving private and public sector partners instituted in a small city in northern Tasmania. The program represents part of a state-wide initiative to challenge the persistence of structural educational disadvantage and what is understood to be an entrenched "culture" that is insufficiently attuned to the necessity of further education. In this paper, we analyse this program from the perspective of key community partners drawing on a series of semi-structured interviews. We offer an analytic framework that suggests an integrated approach to thinking about supporting educational achievement, attainment and retention in regional Australia. It is our view while there is much that regional communities struggling with change can learn from this program, there are conceptual limitations in the way the problem of educational achievement is understood that should be enhanced by a more comprehensive understanding.