Digitization has become involved in every aspect of life, including the healthcare sector with its healthcare professionals (HCPs), citizens (patients and their families), and services. This complex process is supported by policies: however, to date, no policy analysis on healthcare digitalization has been conducted in European countries to identify the main goals of digital transformation and its practical implementation. This research aimed to describe and compare the digital health policies across four European countries; namely, their priorities, their implementation in practice, and the digital competencies expected by HCPs. A multiple-case study was performed. Participants were the members of the Digital EducationaL programme invoLVing hEalth profEssionals (DELIVER), a project funded by the European Union under the Erasmus+ programme, involving three countries (Denmark, Italy, and Slovenia) and one autonomous region (Catalonia-Spain). Data were collected using two approaches: (a) a written interview with open-ended questions involving the members of the DELIVER project as key informants; and (b) a policy-document analysis. Interviews were analysed using the textual narrative synthesis and the word cloud policy analysis was conducted according to the Ready, Extract, Analyse and Distil approach. Results showed that all countries had established recent policies at the national level to address the development of digital health and specific governmental bodies were addressing the implementation of the digital transformation with specific ramifications at the regional and local levels. The words "health" and "care" characterized the policy documents of Denmark and Italy (309 and 56 times, 114 and 24 times, respectively), while "development" and "digital" (497 and 478 times, respectively) were common in the Slovenia document. The most used words in the Catalonia policy document were "data" and "system" (570 and 523 times, respectively). The HCP competencies expected are not clearly delineated among countries, and there is no formal plan for their development at the undergraduate, postgraduate, and continuing educational levels. Mutual understanding and exchange of good practices between countries may facilitate the digitalization processes; moreover, concrete actions in the context of HCP migration across Europe for employment purposes, as well as in the context of citizens' migration for healthcare-seeking purposes are needed to consider the differences emerged across the countries.