This article describes the progression of the Health Insurance Literacy (HIL) Action Team's efforts from the initial charge by the Extension Committee on Organization and Policy (ECOP) of identifying priorities for Cooperative Extension health programming to developing and testing a national mobile messaging campaign designed to change health insurance knowledge, confidence, and behaviors of millennials. It highlights relevant empirical literature, summarizes the results of a national pulse online survey administered to Extension professionals and how they were applied to this project, reviews the Design Thinking and concept mapping process, and describes the development and testing of mobile messages. Anticipated outcomes of the mobile messaging campaign are discussed. Sources of data are the national pulse online survey along with insights gleaned from Extension professionals who participated in workshops, an eXtension Design-a-thon, and responses to a survey of millennials about experiences using health insurance, social media, and texting. This effort contributes to advancing Extension's capacity to deliver programming related to health insurance education in innovative and effective ways.