Orthodox Christian approaches to the sacrament of penance in the seventeenth and early eighteenth centuries are a story of adaptation, reception, and sometimes unintended consequences. In the middle of the seventeenth century, Ruthenian theologians like Metropolitan Petro Mohyla, Ioannikii Haliatovskyi, and Innokentii Gizel’ adapted what they thought useful from the confessional diversity of the Polish-Lithuanian Commonwealth into Orthodox practice. Faced with a different set of challenges, contemporary Moscow-based clerics, including Patriarch Nikon, decided to adapt many of these confession-related changes for their own purposes. In the eighteenth century, Ruthenian hierarchs including Dymytrii Tuptalo and Teofan Prokopovych, alternately emphasized or instrumentalized such notions as the secrecy (‘seal’) of the confession that would become foundational in the Russian empire. The approaches to the sacrament of penance at the turn of the eighteenth century—simultaneously constitutive and transformational—are thus a curious case of histoire croisée, with shape-shifting intercrossing at multiple national and confessional levels.