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Complicated acute diverticulitis (Hinchey III and IV) remains a critical challenge in emergency surgery. Despite evidence favoring primary anastomosis over Hartmann’s procedure, the latter remains widely performed due to surgeon experience, hospital resources, and perceived safety. Trials like SCANDIV, DILALA, LOLA, LADIES, and DIVERTI have shaped current management, highlighting benefits such as reduced stoma rates and improved survival with primary anastomosis. Key factors influencing surgical decisions include patient risk assessment, intraoperative conditions, and surgeon expertise. This presentation explores the latest evidence, guideline recommendations, and real-world cases, reinforcing the importance of tailored decision-making to optimize patient outcomes.