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The article seeks to explicate urban warfare, its intricacies and devastating impact on civilian populations and infrastructure. Historically, many doctrinal manuals were produced emphasising that urban areas should not be added to war zones. However, as the centres of gravity, the cities have always been targets of fighting. Therefore, it is a prevalent thinking that future fights will take place in megacities and dense urban areas. The dynamics of urban warfare are relatively dissimilar from traditional warfare due to the complexity and density of critical infrastructures in urban settings. To unpack the complexity, this article raises following questions; a. Why do some states still prefer to wage urban warfare? b. How has technological sophistication altered the battles in urban areas? The data used for this article is secondary and collected from articles, official and unofficial websites, books and news. The article found that modern technologies and rapid urbanisation have altered the nature of warfare toward urban areas and technological sophistication has fundamentally changed the nature of warfare at strategic, operational and tactical levels. To prove the argument, an instance of the Russian-Ukraine war has been used which presents a clear picture of the conduct of urban warfare and the complexities attached to it. [ABSTRACT FROM AUTHOR]