The advent of the Web has renewed interest in the use of information and communication technologies to support not only virtual communities but also traditional communities. This paper observes that the majority of successful applications to date tend to use technologies to substitute for and/or enlarge existing community interactions and transactions. We argue that this trend, unfortunately, deepens the digital divide between those who have social and knowledge capital and those who don’t. In order to improve the conditions of low-income residents, there is a need to deploy tools that help to reconfigure rather than simply substitute or enlarge existing community interactions. This paper describes the methodology of asset mapping and the development and deployment of a tool called PrairieKNOW (Prairie Knowledge Networks On the Web) in Champaign-Urbana, Illinois’ Prairienet community network. While Champaign-Urbana was ranked by Newsweek magazine as one of the ten most wired cities in the world, it also has a substantial low-income population that has traditionally been under-represented in their use of Prairienet.