This study aims to contribute to the understanding of Russian special operations by analyzing the Battle of Hostomel, the first major airborne assault by Russia’s VDV forces during the 2022 invasion of Ukraine. The purpose is to examine why the operation to seize Antonov Airport failed, despite its strategic importance and the VDV’s elite status. By studying this specific case, the thesis seeks to generate insights into how airborne assaults are planned and executed within the framework of conventional warfare. The analysis is guided by William McRaven’s theory of relative superiority, which identifies six key principles: simplicity, security, rehearsal, surprise, speed, and purpose, that are essential for the success of special operations against a stronger opponent. This study is constructed as a theory-consuming case study that uses qualitative analysis to evaluate the Hostomel operation in light of McRaven’s framework. Utilizing secondary sources from western researchers in war science and literature based on research about the war in Ukraine, the findings show that the VDV operation at Hostomel failed due to shortcomings in several of McRaven’s principles. Poor operational security, limited preparation and rehearsal, and weak coordination led to the loss of initiative. The outnumbered and ill-equipped Ukrainians successfully delayed and disrupted the Russian advance, preventing the establishment of an airbridge and contributing to the broader failure of Russia’s initial campaign against Kyiv.