Waste management in Indonesia faces the challenges of increasing waste generation and has traditionally relied on a linear system focused on waste collection and transportation. Shifting toward a circular economy is imminent as the National Development Plan of 2020–2024 emphasizes integrating circularity in waste management. This chapter describes the transition process in two Indonesian cities, Semarang and Makassar, through case-study analysis primarily using qualitative methodology, including desk reviews, focus group discussions, interviews, and field surveys. The discussions explored the dynamics between actors in Semarang’s waste management system while examining the operational challenges faced in Makassar. Both cases underscored the potential of decentralized waste management through community involvement to enhance waste circularity. Key findings indicate that both cities face common challenges of limited funding and lack of waste segregation, while robust community initiatives and digital platforms could potentially help. In addressing challenges in transitioning into a circular economy, policy and governance reform, community programs, and stakeholder collaboration are the key factors dictating success. Good practices in the waste management activities in Semarang and Makassar include fostering digital initiatives to improve community participation, engaging the informal sector, and enacting the “one neighborhood, one waste bank” policy.