While the transition toward digitalized health care and service delivery challenges many publicly and privately funded health systems, patients are already producing a phenomenal amount of data on their health and lifestyle through their personal use of mobile technologies. To extract value from such user-generated data, a new insurance model is emerging called Pay-As-You-Live (PAYL). This model differs from other insurance models by offering to support clients in the management of their health in a more interactive yet directive manner. Despite significant promises for clients, there are critical issues that remain unaddressed, especially as PAYL models can significantly disrupt current collective insurance models and question the social contract in so-called universal and public health systems. In this paper, we discuss the following issues of concern: the quantification of health-related behavior, the burden of proof of compliance, client data privacy, and the potential threat to health insurance models based on risk mutualization. We explore how more responsible health insurance models in the digital health era could be developed, particularly by drawing from the Responsible Innovation in Health framework.