Iran’s 20th-century prison poetry is a unique phenomenon combining personal anxieties, political protest, and philosophic self-reflection. The article follows the evolution of the genre habsiyat in the context of historical and social changes in Iran. The author, who translates Iranian poetry, identifies four periods within the genre’s development: from the origin of the theme until the Constitutional Revolution, during the Constitutional Revolution, in the tumultuous aftermath of the revolution until the forced abdication of R. Shah, and from the reign of the second Pahlavi until the 1979 Islamic Revolution. Despite obvious changes in their poetics, all habsiyat poems created throughout the aforementioned periods are defined by scathing criticism of political violence and affirm the poet’s increasing moral responsibility. The study offers a closer look at the poetry of M. Bahar, M. F. Yazdi, Nima Yooshij, and M. A. Sales, and explores the symbolism of their oeuvre (‘dark waters,’ ‘the leafless garden,’ ‘snow,’ and ‘autumn’). The article emphasizes the significance of prison poetry as a form of cultural resistance and a mirror of national conscience.