This qualitative research study explores educational leaders’ views on economically disadvantaged families’ perceptions about the relevance of schooling and compares these with government and international educational policy objectives in five regions of the Tanzanian mainland. The findings indicate that economically disadvantaged families devalue schooling. Five indicators supported this argument: 1) parents’ unwillingness to bear the opportunity, direct, and indirect costs of schooling; 2) parents’ reluctance to support school activities and their children’s education; 3) families’ negative perceptions regarding the value and returns from schooling; 4) families’ tendency to purposefully hinder teachers’ efforts to encourage schooling; and 5) parents’ tendency to purposefully urge their children to perform poorly in the national primary school leaving examination. The incongruences between policy objectives and how families, according to educational leaders, understand the relevance of schooling require investigation. While the policies maintain that education is a means of eradicating poverty, the families in the studied rural communities feel that their children’s educational advancement increases household poverty, is a burden, and is an irrelevant strategy for alleviating their poverty. The study concludes by emphasising the importance of the need for alignment in realising education between educational policies, implementers of the policies, and the end-users; collaboration between educational leaders, teachers, and families in enhancing children’s schooling; cultural responsiveness; and the overall quality and relevance of schooling