This paper theorises historical prison escapes by male prisoners from Scottish prisons, arguing that they represent a form of hegemonic masculinity. That dominant masculinity parallels recapture narratives constructed by the official masculinity associated with military service and its transfer to the prison ethos. Manly soldiering cultivated in prison officers with previous military service suited them to security duties. Violence, cunning, determination and athleticism is reflected in the escape bids, and human needs. These escapes occurred before electronic technology secured prison estates, so the strength and vigilance of the prison officers was essential. The sociology of escapes and the prison community literature underpins the paper’s narrative analysis. It is concluded that escape data offers opportunities to understand the material nature of escape processes, and the representation of masculinity as reflected through accounts of technologies implemented in escapes, as well as to how the state represents prison escapes. By connecting masculinity to prison escape processes, a conceptual bridge is created between prison culture and concepts of masculinity. The latter, it is argued, are represented in narrative depictions of escapes. Escape narratives teach us about material forms of legal violence and embrace a tacit recognition of heterosexual manliness.