Urban gaming simulation (UGS) has the potential to create a friendly and engaging environment that enhances participatory urban planning. However, realizing this potential requires an understanding of the pedagogy behind gaming simulation and addressing misconceptions associated with its implementation. This chapter explores the utilization of UGS as a pedagogical tool in the context of urban planning education and participatory urban planning. It argues that UGS offers unique benefits in terms of learning and experiencing the consequences of actions within the game. However, these benefits should not be taken for granted, as they necessitate careful design considerations and effective debriefing sessions. By outlining paradoxes and contradictions that arise in practices, this chapter aims to advocate for a more informed approach to playing and educating through UGS. Drawing on practical experiences and research, the chapter divided the notion of UGS into three realms in response to the Technological Pedagogical Content Knowledge model; a realm of game design, gaming session pedagogies, and the plausibility of urban planning content and context that can be incorporated into simulation games. Ultimately, it seeks to inform real-world practices by translating gameplay experiences into actionable strategies for community and urban redevelopment.