This report investigates the adoption of Agile methodologies, analyzing the complexities encountered in IT projects across different decades. It begins by reviewing five key pieces of literature on Agile adoption, identifying complexities related to traditional methodologies, digital platform dependencies, employee job satisfaction, budgeting and timelines, and project dynamicity. The report then provides a thematic analysis of these complexities, highlighting issues such as the need for business case introductions, organizational transformations, the importance of quality, and the rigidity of traditional functioning. Furthermore, the report examines IT projects from the 1980s to the 2010s, discussing their critical issues, risks, and challenges, including scope, schedule, cost, quality, and the expertise of project managers and teams. The report references various projects such as Pac-Man, Adobe Photoshop, and Facebook, to illustrate how Agile methodologies address these complexities, offering a comprehensive view of Agile adoption in the IT landscape.