Given that street business is conducted in highly place-specific fashions in different countries, the management of street business as an example of managing urban informality is a subject well worth investigating in the context of urban management. Drawing upon theories of decentralized management, this paper examines the ways in which the Taipei City Government regulates street vendors. This study adopts a qualitative method that includes interviews with members of the street vending community and archival research to identify evolving management strategies. Historically speaking, the management of the Shilin Night Market adopted a mixed approach that incorporated the municipality's oversight, the vendors’ organization management, and local proprietors’ management. Specifically, the street vendors’ self-organized entities negotiated (and cooperated) with the Market Administration in a way that eventually allowed them to occupy a formally built interior market. They also coordinated with private landowners to conduct their businesses inside storefront arcades and on street sides. More recently, the Market Administration implemented an arcade vending allocation plan to handle the unlicensed street vendors who had been occupying the streets and arcades since the early 1990s. Though decentralization has historically helped the market to thrive, two primary issues have emerged. The first is the partial participation of dominating interest groups, which prevents a democratic decision-making process and eventually influences the residents’ everyday life experiences in the neighborhood. The second issue results from the established street vendors’ spatial exclusion and territorial control as obstacles to fair resource allocation for newly arriving street vendors. This paper argues that in place-based decentralized management, community diversity and social ecology influence the effectiveness of management outcomes. The conclusions summarize the social and political implications of this study, providing suggestions for urban policy implementation.