Background: The evolution of names, from “medical informatics” to “connected health”, implies that the evolvement of technology in health care has been shifted from technology-oriented to healthcare-oriented implementation. Connected healthcare, a healthcare platform of remote monitoring and self-management through technological measures, is suggested to contribute to the efficiency, cost effectiveness, and satisfaction of healthcare recipient enhancement. However, limited understanding of related connected health (CH) terminology may constrain its implementation. Whether CH is a Buzzword only or a practice that can contribute to an ageing society is controversial. Objective: This study aims to distinguish CH-related terminology and to identify the trend of CH through reviewing its definition, initiation, development, and evolvement, in order to offer management insights and implications. The objective is to understand what is connected and who is cared about in the connected health model, so that better applications can be addressed for the benefit of society. Method: This study reviews the evolution of names, from “medical informatics” in the 1970s to “connected health” after 2000, as well as relevant literature of CH, including e-health, telemedicine, telehealth, telecare, and m-health, to discover the trend of technology-related healthcare implementation. The current status and issues facing CH will be presented and its future trends will be explored through reviewing how changes in healthcare are managed, in addition to its operation and practice. Issues of accessibility, quality, and cost will be discussed, as well as its market status. Results: Preconditions and requirements for implementing CH are identified to select a typical case to study. Areas with a complete business ecosystem, including advanced technology and medical services, a payment system, an ageing population, geographic isolation, integrated health, and social care, are prevalent. These findings may be beneficial to designing and establishing comprehensive CH implantation and environments. Conclusion: The evidence and tendency of technological convergence create a demand for innovation and partnering with start-up companies that offer a competitive advantage in innovation. Specifically, it is necessary to innovate both the public and private operation model of the CH ecosystem. This focus will be further explored in future work.