Despite significant resources employed in the digitalisation agenda in the healthcare sector in Sub-Saharan Africa, the transformative impact of information and communication technologies has not been realised. This article makes two contributions towards developing an understanding of this failure. First, it provides a review of a rich body of academic literature and practitioner accounts regarding barriers to digitalisation and organises them using an established framework. Second, recognising the continuing struggle that digitalisation presents, it proposes a paradigmatic shift in thinking about barriers to digitalisation and suggests the existence of a more fundamental barrier related to inappropriate incentives within the international community. Ultimately, it argues that unpacking the complex contextual reality of healthcare delivery systems is a fundamental but still unaddressed antecedent to any successful digitalisation endeavour. Thus, both the academia and the practitioners should direct their efforts to developing new approaches, which could remove this underlying obstacle.