Abstract Background According to the literature, digital health brings an innovative approach to healthcare and an inevitable transformation and disruption. The potential of digital technologies is far-reaching, from preventive medicine to addressing public health challenges. However, the implementation also significantly depends on the social & cultural context. Methods To research Croatia’s expectations, challenges, and readiness for implementing digital health, interviews were conducted with physicians, patients, hospital managers, policymakers, jurists, and engineers (n = 75). Following identifying key themes, a survey was conducted among Croatian medical students (n = 775) at the end of 2022. Results Key stakeholders believe implementation preparedness is demonstrated through institutional and societal readiness. Prominent characteristics of societal readiness include appropriate infrastructure and legal and financial frameworks. Societal readiness is assessed through digital and health literacy and existing social practices within Croatian society. Only 4.6% of medical students believe Croatia’s healthcare system is ready to implement digital technologies. They perceive the highest readiness regarding digital education (63.7%) and the digital literacy of physicians (60.9%) while negatively evaluating healthcare infrastructure, financial resources, and patient literacy. The results highlight numerous aspects that must be addressed for successful implementation, many of which have been neglected in previous periods. Conclusions The research identifies critical aspects of the social context and presents valuable implications for the digital health transformation. Key stakeholders assess that institutional and societal readiness is not at the level required for the sustainable implementation of digital health, thus necessitating specific actions, ranging from governmental bodies and international organisations to the health system, education system, and media. Key messages • It’s crucial to align digital health implementation with the social & cultural context and capabilities. • The prerequisites for successful implementation necessitate engagement across various societal domains beyond the healthcare system.