Connected Kids project is about developing a searchable database system for the disenfranchised people of the city of Troy, New York. The various events and programs for the young people of the city as created by the various not-for-profit organizations are searched by the parents, kids, teachers, and counselors. Testing the beta version of the tool pointed out that users have found the system challenging to use, though they participated in designing it. Therefore, a new adaptive system with a software agent is proposed to help users effectively perform the tasks without feeling intimidated or unnecessarily overwhelmed by the technology or the tool. The agent’s aim is to understand the real goal of the user and help achieve results that match the needs as closely as possible. The overall strategy is to break up the puzzle into smaller answerable problems and build back the original piece by strewing the smaller pieces.