Digital transformation is changing the landscape of many industry sectors. Healthcare, and health insurers face particularly significant challenges. On the one hand, technical innovations create opportunities; on the other hand, they have disruptive potential. Insurance carriers have to solve key tasks besides the societal problem of rising healthcare costs. They need to digitize their limited customer contact points. Modern technologies offer new solutions to promote healthier lifestyles for insured people and to monitor ongoing treatments. Prevention and monitoring of therapies are thus moving into insurance companies’ sphere of influence. In this way, the health of policyholders can improve sustainably in the long term. The cost burden caused by medical absences and illness is relieved. Effective methods include intelligently using loyalty technologies and customer dialogue through digital and mobile platforms.