As urbanization increases, cities are becoming more strategically important in war, making urban warfare an increasingly relevant field of study. At the same time, research still lacks broadly applicable explanations for tactical success in urban environments. This study aims to test whether Alice Hills success factors can explain the different outcomes of the battles of Sadr City in 2004 and 2008. To answer this question, this study uses a theory-testing approach through a comparative case study with a most similar design and qualitative text analysis. This study shows that the 2004 operation was marked by limited control over the population and the area and insufficient personnel in relation to the size of the city. In contrast, the 2008 operation fulfilled more of Hills success factors, including more effective use of combined arms and a stronger control of the operational area and the population. Overall, the results indicate that Hills theory can largely explain the different outcomes and remains analytically useful for understanding tactical success in urbanwarfare. The findings also further support the notion that Hills framework, while not yet a complete theory holds significant analytical promise. Further theory-testing across different conflict types and modern cases, such as Ukraine, is needed to broaden the theory’s empirical foundation.