Recently, there have been some attempts to reframe the Augustinian view of political realism in terms of the Foucauldian concept of resistance and discipline; attempts which resonate with another Foucauldian, post-colonial understanding of Augustine. This paper addresses both political realist and post-colonial ‘Foucauldian approaches’ to Augustine, examining how Augustine envisages critical resistance and counter-disciplines in the midst of the earthly city’s domination. Redefining political realism as the tragic ambiguity of healing intermixed with disease, it will examine how Augustine allows (and offers) social criticism of the earthly city’s ethos, civic rituals and networks of disciplinary power, not least through the heavenly city’s counter-disciplines, including the sacraments, oration, rebuke, coercion, and civic virtues. It is argued that, as Augustine’s understanding of social criticism and counter-discipline is concerned with spiritual freedom and the effect of grace, it does not collapse into support for disciplinary measures of human control.