Background/Objectives: Globally, life expectancy has been increasing with South Korea focusing on improving health to enhance quality of life. The COVID-19 pandemic further emphasized the need for digital transformation in healthcare, accelerating digital health adoption. This study explores the digital divide between ‘Digital Natives (20–39 Y)’ and ‘Digital Immigrants (40–69 Y)’, focusing on digital device usage and confidence. Methods: This study utilized national survey data from the Digital Health Literacy Survey Results and Policy Implications, focusing on differences in digital device use and confidence between young adults (20–39 Y) and middle-aged adults (40–69 Y). The participants comprised 1000 adults aged 20 to 69 in the Republic of Korea. Respondents were queried about their use of digital health tools, such as wearable devices and mobile apps. Confidence in using digital systems and managing health via digital tools was assessed using a five-point Likert scale. Results: The findings indicated that while young adults have lower rates of using digital devices for healthcare, they exhibit higher confidence in using such devices. In contrast, middle-aged adults, despite having lower confidence, report higher usage of digital devices for healthcare purposes. Conclusions: This study explored differences in digital confidence and healthcare usage between age groups and aimed to propose effective health management strategies based on digital accessibility.
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