This article investigates how civic discourse connects the virtue of citizens and the fortunes of cities in a variety of late antique and early medieval sources in the post-Roman west. It reveals how cities assume human qualities through the rhetorical technique of personification and, crucially, the ways in which individuals and communities likewise are described with civic terminology. It also analyzes the ways in which the city and the civic community are made to speak to one another at times of crisis and celebration. By examining a diverse range of sources including epideictic poetry, chronicles, hagiographies, and epigraphic inscriptions, this article addresses multiple modes of late antique and early medieval thought that utilize civic discourse. It first explores how late antique and early medieval authors employed civic discourse in non-urban contexts, including how they conceptualized the interior construction of an individual's mind and soul as a fortified citadel, how they praised ecclesiastical and secular leaders as city structures, and how they extended civic terminology to the preeminently non-urban space of the monastery. The article then examines how personified cities spoke to their citizens and how citizens could join their cities in song through urban procession. Civic encomia and invective further illustrate how medieval authors sought to unify the virtuous conduct of citizens with the ultimate fate of the city's security. The article concludes with a historical and epigraphic case study of two programs of mural construction in ninth-century Rome. Ultimately, this article argues that the repeated and emphatic exhortations to civic virtue provide access to how late antique and early medieval authors sought to intertwine the fate of the city with the conduct of her citizens, in order to persuade their audiences to act in accordance with the precepts of virtue.