Purpose. To understand how digital technologies can help healthcare organizations to improve the exploration-exploitation paradox over time. We explore antecedents, processes, and outcomes of implementing digital transformation programs. Design/methodology/approach. Primary sources come from 107 semi-structured interviews with key informants within 14 Italian hospitals between 2009 through 2011. The definition of a taxonomy of digital solution thanks to the contribution of 60 practitioners followed. The case study method has been applied in order to analyse 14 Italian hospitals with embedded unit of analysis: 1) digital transformation processes; 2) hospitals; 3) regional healthcare systems. Findings. Three complementary paths emerge as fundamental to paradoxically balance exploratory and exploitatory efforts in healthcare: (i) assets digitalisation within hospitals; (ii) digitally-based process integration; (iii) disruptive decision-making through analytics. Intra- and inter-path characteristics are discussed to show how digital transformation can both move hospital within the exploration-exploitation space. Research limitations/implications. By its very nature, this study is exploratory and notwithstanding the number of cases and interviews, its generalizability is limited. Practical implications. Digital transformation programs are a fundamental resource to resolve the tensions raised by the exploration-exploitation paradox. Their implementation leads to better performance (cost reductions, quality improvements). A framework is provided in order for practitioners to make better decisions. Originality/value. This study sheds new light on how digital technologies are actually adopted and adapted in healthcare contexts. It does it by entailing a longitudinal perspective.