ABSTRACT Motivated by the prevalence of an aging population and the associated increase in chronic diseases, coupled with rising medical expenditure, the Korean government initiated a pilot project in Pyeongchang-gun, Gangwon-do, a rural area, to implement a “smart online-to-offline (O2O) digital health care model” aimed at managing and preventing chronic diseases. However, there is limited understanding regarding perspectives and levels of preparedness for digital health among stakeholders at various levels. In-depth focus group interviews were conducted with elderly and non-elderly community members, health care providers, and staff members at Pyeongchang Health and Medical Center. The study found the presence of both positive and negative perceptions and a lack of preparedness across different levels. At the end-user level, it was observed that community members, especially the elderly, have low levels of health and digital literacy, compounded by limited access to social support. At the health care provider level, there was uncertainty about the acceptance of the digital health program. At the area level, the need to bolster health staff members and enhance their capacity was observed. Recommendations include: customizing the design of the online and offline service components by considering end-user factors (such as age, occupation, and household type) that may contribute to disparities in health; establishing a platform for providers to share their experiences to facilitate the effective incorporation of digital health into their practices; and preparing an appropriate provider payment mechanism.