Health workers, especially auxiliary nurse midwives (ANMs), are among the most critical resources in improving the quality of immunization services and reducing vaccine hesitancy under the Universal Immunization Programme (UIP) in India. To improve health worker immunization skills, UIP trainings in India are primarily conducted through instructor-led classroom, cascade trainings. However, a 2018 capacity-building need assessment revealed several challenges involved in traditional classroom training, such as a single-time exposure to new guidelines, complicated logistics arrangements, a lack of refresher training, and varying quality of training. These complexities make it difficult to meet the timely knowledge and skill needs of every health worker effectively and uniformly in a rapidly changing scenario of UIP. To meet health worker capacity-building needs and address these challenges, Rapid Immunization Skill Enhancement (RISE), a learning management system (LMS) application, was conceptualized. The RISE LMS application was developed as a human-centered, interactive, continuous, and adaptable knowledge and skill-building platform for health workers engaged in the UIP. RISE complements existing classroom-based cascade training for health workers by leveraging digital technologies for faster, easier, and more effective knowledge transfer to accommodate the fast-changing needs of a dynamic health program like UIP. In this article, we share the challenges and strategic solutions to digital training applications, lessons learned, sustainability of the application, and the impact RISE has made in India, all of which stemmed from leadership, coordinated efforts from a team of skilled professionals, government acceptance, detailed planning, and continued stakeholder engagement.