Complex Information and Communication Technology (ICT) applications dedicated to support the provision of community-based services can rarely be implemented by single social services agencies. Technical and funding requirements make it almost prohibitive for such agencies to undertake them in isolation. Furthermore, in the social sector the degree of service interdependence within a community makes it almost necessary that such complex systems be implemented in collaboration as a community-based initiative. But implementations in this context are filled with challenges not normally found in single institutional ICT projects, making community-based ICT initiatives paradoxical and difficult to manage only with conventional project management techniques. This chapter compares ICT management in various sectors. Using the case of Homeless Management Information Systems in the United States, the chapter presents some complexities involved. It then presents a model for understanding the contrasting opposing forces at play in the social sector and offers implementation management recommendations to increase the likelihood of their success.