Notions of the smart city look to mobilize information technology to increase organizational efficiency, and more recently, to support new forms of community engagement and involvement in addressing municipal issues. As cities turn to civic enterprise technology platforms, we need to better understand how that class of system might be positioned and used to collaborate with informal community-born coalitions. Beginning in 2019, we undertook an embedded collaborative research project in Albany Georgia, a small rural city, to understand three primary research questions: (1) How do community organizing practices take shape around joint initiatives with local government? (2) What data, tools, and process are needed to support those initiatives? (3) How do the affordances of City-run enterprise platforms support such community-born initiatives? To develop insight into these questions, we deployed a mixed-methods study that interwove participant observation, qualitative fieldwork, and participatory workshops. From this, we point to several mismatches that arose between the assumptions of a managed enterprise environment and the complex needs of establishing and supporting a multiparty community coalition.