The study devoted to the initial coinage of King Władysław Jagiełło is of particular relevance due to the insufficient attention paid to the complex interrelations between monetary policy, urban institutions and the nobility. The aim of this work was to identify the key features of Jagiełło’s first coinages. To achieve this, an interdisciplinary analysis of numismatic, archival and archaeological sources was employed. Two unique coins discovered in Ukraine are described, which, in the author’s view, represent the first emissions of King Władysław II Jagiełło struck in Vilnius and Wschowa. The research revealed that the new denominations introduced at the beginning of Jagiełło’s reign were closely linked to the policy of unifying currency circulation and the king’s aspiration to ensure a stable emission mechanism. The coin finds and documentary records confirmed that the quality and fineness of silver could fluctuate depending on the resource base and the conditions of specific mints.