Recent technological advances make possible a practical, rigorous application of communities of interest (COIs) to redistricting measures. Geographers, political scientists, and legal scholars have suggested that keeping communities together can enhance representational fairness. As other paths for redressing gerrymandering have closed in recent years, communities of interest provide a key legal criterion to guard against partisan and racial motives in redistricting. However, the existing literature on communities of interest is fractured between differing conceptions of the term as well as concerns of subjectivity in the identification of communities. We advocate for a novel approach that encompasses a theory of community-based political representation as well as practical, technologically innovative methodology for documenting communities of interest. Specifically, two quantifiable standards—the Effective Splits Index and the Uncertainty of District Membership—can be leveraged to judge the degree to which a community of interest has been split. By equipping citizens with these new tools, technology can provide a workable and rigorous standard for use of communities of interest as a criterion for fair districting.