This talk presents and explains Health Web Science, Health Web Observatories, and the technologies needed to create and utilize them as an approach towards preferable health outcomes in the 21st century. Health Web Science (HWS), which impact of the Web on health and wellbeing, aims towards a preventative, participatory, personalized, and predictive (P4) model of healthcare. HWS posits this can be achieved by the leveraging of the Web’s data, resources and nature. In studying the Web, it is impossible to ignore the evolving social, political, economic, policy questions that emerge as a result of the use of the Web. Health Web Observatories play a role by enabling the study of these data, make available the metadata, and thereby enable it as a feedback mechanism for preferable futures.