This chapter explores the evolution of legal prohibitions on castration within the Roman and Byzantine empires, focusing particularly on a novel (NL. 60) issued by Leo VI (886–912). While early Roman emperors, from Domitian (81–96) to Justinian I (527–65), enforced strict bans on castration—imposing severe penalties such as deportation, confiscation, and even death—Leo VI introduced a nuanced approach. Although the novel maintained the general stance of prohibition, it notably tolerated certain forms of punishment, marking a departure from prior rigidity. The chapter contextualises this legal shift within the broader reforms of penal law initiated by Basil I (867–86) and Leo VI, suggesting an effort to recalibrate the relationship between crime and punishment. Moreover, it examines ecclesiastical perspectives, focusing particularly on canon 8 of the Council of Constantinople (861), where the presence of the eunuch patriarch Ignatios may have shaped the discourse on castration. Through a comparative analysis of civil and canon law, the study investigates the interplay between imperial legislation and ecclesiastical canons. This chapter also examines the impact of NL. 60 on the practice of castration in the empire, which involves an analysis of the long-standing contradiction between the prohibitions on castration and the imperial use of eunuchs.