The Macedonian era (867–1056), particularly under Basil I (867–86) and Leo VI (886–912), marked the most productive period in Byzantine legal history following the death of Justinian I. The emperors undertook a major codification project aimed at restructuring earlier legal provisions, resulting in three texts: the Prochiron, the Eisagoge, and the Basilica. Notably, these works incorporated the majority of the Justinianic provisions concerning eunuchs and castration, in contrast to the earlier Isaurian project, which largely omitted such issues. Leo VI also issued new legislation, three of which specifically addressed matters relating to eunuchs. These Macedonian laws suggest both a legal transmission of the Roman legal tradition from Justinian I’s reign and a response to evolving social realities concerning eunuchs. This chapter conducts a comparative analysis to explore how and why the legal status of eunuchs or infertile men was both transformed and preserved between the reign of Justinian I and the Macedonian dynasty. It shows the context and content of the legal projects undertaken by Basil I and Leo VI, highlighting their difference from those of Justinian I and the Isaurian emperors. The chapter concludes with an overview of the situation of the eunuchs during the period and evaluates how earlier provisions were accepted during the Macedonian era.