Purpose According to the Kaiser Family Foundation (2014), 502,866 (11.7 %) of Florida children under 19 years of age are uninsured, giving Florida the second largest number of uninsured children in the United States. Florida Covering Kids & Families (FL-CKF) is dedicated to developing innovative outreach methods for enrolling and retaining eligible children in Florida KidCare, the state's Children's Health Insurance Program. FL-CKF has developed a strong data system that allows it to evaluate the effectiveness and success of statewide enrollment and retention efforts. Description The data system was created using the Checkbox survey systems. Community and school outreach partners enter data each month on all completed Florida KidCare applications via a secure interface. The system requires data be entered in a uniform format and forces vital data points to be completed. These data are then transmitted to the state to obtain timely application determination information on enrollments. Assessment The data system helps FL-CKF to determine which outreach strategies are successful and where changes need to be made to increase effectiveness. The system also provides feedback to community outreach partners in order to enable follow up with families when needed. Conclusion Organizations helping uninsured children apply for health insurance may benefit from creating data collection systems to monitor project efficacy and modify outreach and enrollment strategies for greater effectiveness.