Many insurers have hesitated for some time to migrate their data and applications to the public cloud because it implied moving sensitive information and capabilities outside of the organization’s control. However, these concerns have decreased as insurers gained more confidence in vendors as they acquired more experience—and as cloud has established itself as an indisputable key component of an insurer’s digital transformation journey. The Model Insurer case study of West Bend Mutual Insurance (WBMI) illustrates some of the challenges and strategies to move workloads to the cloud, as well as the benefits of cloud migration.