The Organization for Security and Cooperation in Europe (OSCE) has made significant progress as a watchdog in advancing media freedom in Serbia while facing limitations in promoting media freedom in Russia. Serbia and Russia share a communist background with numerous media freedom violations. This thesis analyzes the conditions impacting the effectiveness of the operations of the OSCE on media freedom as part of a broader human rights agenda. A centralized goal of this research is to examine differing roles and outcomes of OSCE in Serbia and Russia to show that the organization's ability to effectively promote media freedom depends on organizational characteristics and geopolitical conditions. The OSCE has been restricted from entering Russia to promote media freedom but works in a variety of capacities in Serbia. The OSCE's activities to support media freedom appear most successful when a field mission is present to create active personal involvement in necessary situations.