In the mid-nineteenth century, along with the Ottoman centralization and standardization processes of the Tanzimat (reform) era, the Istanbul Armenian Patriarchate aimed to centralize and standardize marriage practices among Armenians in the empire. In particular church regulations targeted to reinforce the prevention of second marriages, which people often used as a means for divorce. Unlike in Islamic Sharia law, divorce as a legal category was absent in the Armenian Church’s legal canon. Other regulations included forbidding marriage among relatives, among underage boys and girl and reinforcing the church as a singular authority in the legitimization of marriages among Armenians. Yet, Armenians throughout the empire used the legally pluralistic and multi-confessional setting in which they inhabited to cross the legal and confessional boundaries of the Armenian Apostolic community. Armenians used not only Kadi courts (Islamic courts) and the Ottoman government to initiate or end a marriage, but they also used the assistance of Kurdish Sheikhs, local Protestants and Catholics in order to initiate or end marriages that the Armenian Church regulations forbade them to do. The existence of different centers of the Armenian Church, such as the local prelacies and the Edjmiatzin Armenian Catholicosate (the highest office of the church) in the Russian Empire, provided an additional medium for trespassing marriage law. Through the use of petitions sent to the Istanbul Armenian Patriarchate, to the Ottoman government, as well as judicial reports of cases regarding marriage, this paper explores the myriad ways in which Armenians transgressed the legal and communal boundaries to fulfill their individual or family interests. This allows us to detect the agency of Armenians in the Ottoman Empire who are often presented as victims and therefore lack agency in the existing historiography. The paper argues that such individual actions in their collectivity posited a significant challenge to the rigid millet system that the Ottoman government and the Armenian Church aimed to impose. In this system—that never fully materialized—what were considered communal administrative matters, such as marriage, had to be dealt with strictly within the religious code and confessional boundaries of each community.