Remote Australian schools face complex contextual issues due to systemic and enduring disadvantage. The structures and systems put in place to support and provide advantage for Indigenous Australians continually fail to meet their mark due to colonial structures, policies and inability to understand remote contextual demands. In South Australia, the context of this paper, systemic disadvantage disproportionately affects Indigenous people. This article explores the contemporary colonial landscape of a remote school context, provides background on the colonial institutions which shape the interactions and services provided to people in remote Australian areas, and provides two empirical examples of the contemporary, structural, and harmful influence of policy and political figures in a remote school. By examining the politics of being a school leader, the policy background for remote Australian schools, and the unique challenges of position both in policy and physical terms, we show how contemporary racism structures and conditions the lives of young people in remote contexts today.