Shortly before Velika Župa Dubrava witnessed its collapse within the Independent State of Croatia (NDH) in October 1944, the inhabitants fell victim to ceaseless clashes throughout the year and fierce terror on behalf of all warring parties, plunder, killings of innocent civilians and the burning of houses. Famine and shortage of goods due to irregular transport and a general halt of all economic activities threatened to take its toll. The authorities of Velika Župa Dubrava did their best to improve the conditions, although they had no control over a significant portion of the territory occupied by the Četniks, nor were they able to exert any authority on the territory under their own military and police control because the German occupation forces were in full command. The organisation of public administration on the territory of Velika Župa Dubrava testifies to the authority’s efforts to cope with all the administrative issues systematically, yet the lack of professional staff and the prevailing adverse circumstances proved a crucial impediment. Constant crisis marked by military incidents caused deep anxiety and distrust among the inhabitants, which deteriorated by the German retaliation, especially by the deportation of all men from Korčula and Pelješac. This contributed to an increasing support of the partisan movement and their frequent illegal actions, such as the distribution of pamphlets, writing of graffiti and the assassination of distinguished executives of Velika Župa Dubrava. The air raids by the Allies further deepened the calamity, whose bombing of Dubrovnik and the wider city area caused great material damage. Under the mentioned conditions, the collapse of Velika Župa Dubrava in October 1944 followed as a natural and anticipated outcome.