Chapter 5 investigates the decision-making processes behind the challenges of implementing Olympic Agenda 2020’s urban-related Reforms, focusing on insights from field visits and stakeholder interviews for the Paris 2024 and Milan-Cortina 2026 case studies. Building on the Research Agenda developed in Chapter 4 , this chapter transitions to confirmatory research to address the question “what factors led to the stakeholders’ decisions behind the issues compromising Olympic Agenda 2020?” The analysis identifies ten critical Olympic Agenda Glitches, including topics such as “Marketing vs. Sustainability”, “Transparency and Communication”, and “Olympic Exceptionality”, which reveal structural inefficiencies of Games planning compromising the Agenda’s theoretical goals in real-world applications. Conflicting stakeholder priorities, systemic governance issues, and local political dynamics emerge as key contributors to these challenges. By exploring the social, political, and logistical complexities that influence outcomes, the chapter underscores the limitations of top-down policies in addressing context-specific issues. It highlights the need for adaptive governance frameworks and inclusive stakeholder engagement to overcome these obstacles. The findings provide a deeper understanding of how competing interests and structural constraints hinder the Agenda’s urban-related Reforms, setting the stage for Chapter 6 ’s policy Proposals to mitigate these Glitches and enhance the Games’ alignment with sustainability objectives.