Olympic Agenda 2020 was introduced as a transformative framework to align the Olympic Games with contemporary sustainability, cost-efficiency, and legacy objectives. This chapter investigates misalignments between its urban-related measures and their implementation in the preparations for Paris 2024 and Milan-Cortina 2026. By addressing the question “what issues during Olympic Games preparations compromised the Olympic Agenda 2020 strategy?” the chapter employs an exploratory case study analysis to compare the previously systematised Agenda’s Reforms with real-world practices. The findings reveal critical challenges, including misaligned legacy planning, environmental trade-offs, governance inefficiencies, and stakeholder conflicts, all shaped by local contexts. These discrepancies highlight the complexity of adapting the Agenda’s principles to diverse urban and regional realities. To structure further analysis, the chapter develops a Research Agenda comprising 35 Questions focused on areas such as venue classification inconsistencies, resource inefficiencies, and political compromises. It also underscores the importance of addressing these misalignments to achieve the Agenda’s objectives, laying the groundwork for confirmatory research in Chapter 5 , which explores the underlying structural causes of these challenges.