<p>Rewilding has emerged as a significant ecosystem restoration strategy in recent decades with wide variation in design, construction, and management approaches depending on site contexts and the types of human engagement. In Singapore, rewilding projects have been successfully implemented with the inclusion of public and expert groups to meet the state’s greening policies towards increasing urban biodiversity. Despite the apparent success of these initiatives, questions remain: What are the definitions and interpretations of rewilding projects in Singapore? Do rewilding efforts in Singapore fully utilize community and public volunteerism, and, inputs from expert groups in plant science, biology, and design disciplines? Are they merely taming vegetation or fostering dynamic ecosystems towards cultural goals of rewilding? What are suggestions for future rewilding projects? This article addresses these knowledge gaps by exploring the types and degrees of stakeholder involvement and partnership in rewilding projects, examining how they integrate natural processes with human involvement; determine the extent of collective human participation; and consider the cultural, educational, and social values associated with rewilding initiatives. More specifically, the history of development and implementation processes in five distinct rewilding projects is explored, highlighting challenges encountered and lessons about long-term “ecology with cities” engagement, including the roles of individuals from various disciplines in increasing ecological appreciation and environmental stewardship. This article concludes by highlighting the need for adaptive, interdisciplinary approaches and active community involvement to guide future rewilding projects toward lasting ecological and cultural impact.</p>