The marriage of Anne, Duchess of Brittany, to Maximilian I, Holy Roman Emperor, by proxy was a crucial event in the political landscape of late 15th-century Europe. Anne was a woman of considerable influence, as her marriage alliances could shape the destiny of nations. Maximilian I, seeking to enhance his own power and solidify his authority, viewed the marriage as an integral step in extending his influence into Brittany, a region that had the potential to shift allegiances between France and the Holy Roman Empire. The proxy marriage ceremony held in Brittany involved an envoy representing Maximilian who stood in for the emperor, signaling the importance of this diplomatic arrangement. This marriage was fueled by the backdrop of increasing tensions between France and Brittany. At the time, Brittany was embroiled in a struggle to maintain its autonomy from France, and aligning with Maximilian posed a strategic opportunity for Anne to secure support against French advances. Additionally, the wedding carried implications for the future succession of Brittany, as it was envisaged that a pro-imperial rulership would stabilize the region amid the regional power plays of France and England. However, the marriage was not without its challenges. Although it was celebrated, the actual union faced numerous complications, primarily due to the French monarchy's ambitions and the unfolding political dynamics that would eventually lead to the annexation of Brittany into France. The marriage thus set the stage for a complex interplay of feudal loyalties, royal ambitions, and the ever-shifting alliances that characterized the turbulent era in which Anne lived.