This paper draws together data from two projects on schooling dis/engagement in Australia. One project focused on mainstream schools and the strategies employed to retain and engage young people in learning, whereas the other explored the growing sector of alternative/flexible education for similar solutions. We found interesting parallels. For example, rich, relevant curricula delivered through innovative pedagogies alongside positive staff/student relationships were key elements in schooling engagement across both sectors. Those findings have been published elsewhere. This paper focuses on the contributions to schooling engagement that may be derived from mutually beneficial school/community relationships. Here, we examine one mainstream high school and one flexi secondary school, both situated in remote geolocations, that established bespoke school/community partnerships in response to local needs. The data from each site provide blueprints for other schools that wish to tap into the wealth of human and material support systems in their own local areas.