We describe the steps taken by the Harlem Health Promotion Center to develop a community-specific health web portal aimed at promoting health and well-being in Harlem. Methods and results that begin with data collection and move onto elucidating requirements for the web portal are discussed. Sentiments of distrust in medical institutions, and the desire for community specific content and resources were among the needs emanating from our data analysis. These findings guided our decision to customize social software designed to foster connections, collaborations, flexibility, and interactivity; an “architecture of participation”. While we maintain that the leveraging of social software may indeed be the way to build healthy communities and support learning and engagement in underserved communities, our conclusion calls for careful thinking, testing and evaluation research to establish best practice models for leveraging these emerging technologies to support health improvements in the community.