Chapter 6 presents six Proposals to address the Glitches identified in the urban implementation of Olympic Agenda 2020, advancing the sustainability and legacy of the Olympic Games. Using a research-by-design methodology, the chapter answers the question “what measures can be taken to prevent critical issues from recurring in future editions and better ensure the achievement of the Agenda’s goals?” The Proposals include adapting the Olympic Programme to host city contexts, aligning participants’ expectations with urban resources, improving planning processes to mitigate risks, formalising the Games’ role within political structures, engaging local communities, and leveraging the two-staged candidature process to implement these measures. Each Proposal targets issues such as sustainability, governance, transparency, and community engagement, reshaping relationships among the IOC, organising committees, and local authorities to foster collaboration and resilience. By balancing ambitious goals with practical constraints, the chapter underscores the importance of creating a planning framework that aligns the Games with host cities’ long-term development objectives. These Proposals aim to prevent negative impacts that lead to public opposition and erode trust, ensuring that future editions contribute positively to urban sustainability while enhancing public acceptance and the credibility of the Olympic Movement.