Underpinned by stakeholder and agency theories, this study adopts a qualitative multiple-case study approach to explore and analyse various stakeholder interests and how they affect digitalisation in the health sector of a developing country (DC). The study's findings revealed that four key stakeholder interests - political, regulatory, leadership, and operational - affect digitalisation in the health sector of DCs. Further, the study found that operational and leadership interests were emergent and were triggered by some digitalisation initiatives, which included, inter alia, the use of new eHealth software and the COVID-19 vaccination exercise, which established new structures and worked better through digitalisation. Conversely, political and regulatory interests were found to be relatively enduring since they existed throughout the pre- and post-digitalisation eras. The study also unearthed principal-agent conflicts arising from technological, organisational and regulatory factors that contribute to the paradoxical outcomes of digitalisation in the health sector.