The availability of digital competencies among the population in the regions is one of the critical drivers of technological transformation of the medical sector in the coming decades. This article aims to examine the impact of medical digital skills of the population on self-assessment of personal health, satisfaction with healthcare services, and subjective well-being related to health. Using microdata from Rosstat’s 2023 databases on digital competencies and population health status, we calculate indicators of human, health capital, and well-being across population cohorts segmented by five-year age intervals. The findings reveal that medical digital skills positively impact self-assessment of health primarily among individuals aged 50 and older. In contrast, for younger cohorts (aged 20–35), greater engagement with digital health services correlates with poorer health outcomes. Notably, among the various predictors of digital skills, only the use of online platforms for scheduling medical appointments consistently shows a positive impact on both health self-assessment and subjective well-being. While digital support for regional healthcare reforms offers some benefits, its overall effectiveness in enhancing health capital remains limited. Further investments in technological infrastructure and equipment for the healthcare sector are necessary to fully realize the potential of digital transformation.