Background: Digital technology is increasingly being used to enhance various aspects of health care. In the area of community-based, it is important to understand the circumstances and challenges of deploying this technology to solve health care issues. Objective: To develop a tool to support communication and care coordination efforts of community-based prenatal care coordinators who serve low-income pregnant women, and to uncover barriers and facilitators to the tool's use before a wide-scale pilot study. Methods: We devised a four-step development and evaluation process: (1) state-wide stakeholder collaboration to conceptualize the system; (2) expert panel to identify key functionalities to support care coordination and communication between communitybased health workers and pregnant women; (3) iterative and incremental development using agile design and software development; and (4) two evaluations to test usability and user acceptance of the system using real-life scenarios. Results Participants found the web app easy to use and envisioned many benefits of using it in their practices. From the qualitative data, we uncovered many barriers around implementation of the technology, including care coordinator's lack of motivation to participate in the study and provide feedback on the system design. Conclusions: This research provides a methodology for development and deployment of a web-delivered technology in community-based setting. In addition, the research provides insights on real-life challenges of deploying a technology-based solution in communitybased settings.