The main objective of this dissertation is to analyze the complex relations between the Dubrovnik Republic and the Bosnian eyalet (province) during the rule of the Bosnian beylerbey (governor) Hekimoglu Ali Pasha. In order to provide the basic framework and a broader perspective, the political and economic circumstances of the peripheral Ottoman province of Bosnia and a biography of the Ottoman statesman Ali Pasha were reconstructed. In this context, a secondary research objective, regarding the incorporation of the Bosnian eyalet and the administrative achievements of Ali Pasha into the global trends of the Ottoman Empire, was set. Comprehensive review of the political and economic changes in the Bosnian eyalet as well as Ali Pasha’s military and administrative efforts indicates that the periodization, classification and generalization of history reencounters unexpected exceptions and exclusions. Dubrovnik-Ottoman relations were evaluated according to the paradigm of the “soft power” of the Dubrovnik Republic and the “hard power” of the Ottoman Empire. In this context, the soft power of information, services, and diplomacy, employed by Dubrovnik in order to neutralize the hard economic and military power of the Ottomans, was clarified. Although wise and skilful Ragusan diplomacy retained an indisputable role in the favourable outcome of the disputes with the Ottomans, the success of Dubrovnik's missions at the Bosnian court depended on the character of the Ottoman party at the negotiating table. Thus, the research presented here encompasses the gradual development and change of Ali Pasha's personality in the course of his political maturation, which is clearly reflected in relations with Dubrovnik. Disputes form the backbone of Ottoman-Dubrovnik relations. By analyzing the diplomatic efforts of the Dubrovnik Republic at all three levels of the Ottoman administrative system (the Porte – provincial governor – local officials), the Ottoman levers of power and their compliance with long-standing Dubrovnik privileges were discussed. Comparison with the earlier period (15th and 16th century) demonstrated the shift of Ottoman instances responsible for dispute resolutions. The analysis of those complex relations between the Dubrovnik Republic and the Bosnian governor Ali Pasha illustrated the interests that bound them together as well as the stages of their relations due to the strengthening of the Austrian Empire in their neighbourhood. Furthermore, sketches of life in the borderlands during Ali Pasha’s reign provide a vivid picture of Dubrovnik-Ottoman coexistence, which was characterized by dynamic interactions between people of different religion, culture, identity and values. Detailed insight into the fifteen-year sequence of relations between the Dubrovnik Republic and the Bosnian eyalet during Ali Pasha’s reign is based on the fruitful Ottoman-Dubrovnik correspondence kept in the State Archives of Dubrovnik. Other than that, the research presented here was occasionally supplemented by archival sources stored in the State Archives in Zadar, the Archives of the Franciscan monastery in Makarska, the Sarajevo Historical Archives, the Archives of the Herzegovina-Neretva Canton in Mostar, and the Ottoman Archives of the Prime Minister’s Office in Istanbul. Among the mentioned archival materials, the Ottoman documents should be highlighted as they provide insight from the other, often neglected, Ottoman side. On the other hand, documents of Dubrovnik provenance provide a broader historical context and facilitate understanding of the content and spatiotemporal specificity of the Ottoman documents. The interweaving and complementing documents of both provenances allow for a comprehensive picture and balanced approach to the study of Ottoman-Dubrovnik relations.