During Augusto Pinochet’s dictatorship in Chile (1973–1990) political prisoners played, listened to and taught music. Survivors’ testimonies describe musical practices that reveal and reflect the complex political and social realities of their incarceration. Authorities actually used music to torture and degrade prisoners, but for the prisoners, music was also a tool for communication, community-building, catharsis and entertainment. The question of who could choose, play and hear music in these spaces reveals narratives of resistance and oppression, and of the complexities of musical taste in relation to social status, education and political affiliation. The close relationship between left-wing politics and music, in particular the ‘Nueva Canción Chilena’, meant that political prisoners shared a political and cultural identity. This article discusses how political prisoners negotiated musical practices among themselves, with guards, religious figures and common prisoners, drawing on the Cantos Cautivos, a digital testimonial project that documents musical memories of Chilean political prisoners. I argue that political prisoners applied democratic ideals in coherence with their left-wing beliefs, yet through music reproduced some of the social structures of Chilean society. The musical practices in prisons during the dictatorship were, therefore, unique to this body of political prisoners and their political, social and cultural background.