This paper argues that certain taken-for-granted features commonly found in schools can create regimes that are inimical to democracy and the principles of a liberal education for all. Schools in England can be theorized as particularly oppressive institutions that create the conditions that make their children the unhappiest amongst the industrialized nations, generating precisely the disaffection with schooling that they then criticize and punish. They do this through institutional processes that are politically ideological rather than pedagogical. Four distinct features of schooling that synergize in a negative way are compulsion, compression, control, and competition. In presenting this model, the paper notes the demise of the anti-schooling debates of the twentieth century in the contemporary setting in England and other industrialized nations, and argues that the schooling system is needlessly harsh, especially for a substantial minority of young people. The paper draws upon media reports and adjacent research to conclude that compulsory schooling without debate allows punitive authoritarianism to thrive.