This study examines crisis management initiatives undertaken by the OSCE and other actors in the run-up to Russia’s full-scale invasion of Ukraine in February 2022. These efforts—including the Geneva Statement, the OSCE Roadmap, the Normandy Format, the Trilateral Contact Group, the Minsk agreements, and the activities of the OSCE Special Monitoring Mission—unfolded against a backdrop of escalating armed violence and Russian political maneuvers aimed at undermining Ukrainian sovereignty. Despite this sustained engagement, the OSCE’s facilitation and mediation efforts proved insufficient. By analyzing the inherent shortcomings, missed opportunities, and limitations of these diplomatic initiatives, this paper seeks to draw key lessons for improving future international conflict resolution efforts.