This chapter summarises findings from an empirical study investigating how digital healthcare solutions should be developed to satisfy individual demands for understanding and managing healthcare information and activities. Despite the quick development of new digital healthcare services to accomplish service efficiency and cost-effectiveness, and at the same time supporting the achievement of a wide range of sustainable development goals, some users perceive challenges due to different age-related, physical, and cognitive starting points. The chapter offers a broad view of the development of digital healthcare solutions and considers literature and the perspectives of technologists, caregivers, and users through a qualitative approach using interviews and autoethnography. A main finding is that the development of digital healthcare solutions that enhance health literacy needs a comprehensive strategy, in which users, healthcare providers, family members, and other stakeholders should participate.