South Africa has taken the first steps in implementing a National Health Insurance (NHI) scheme. An electronic health record (EHR) system will form a vital component of the infrastructure that needs to be put into place for managing healthcare services. Even a brief review of the literature reveals that managing the transformation from a paper-based to an electronic based system is complex in nature, as it entails a fundamental change in the healthcare culture. Consequently, in many instances such systems do not fully realise the benefits and objectives envisaged. With this in mind, this research study focuses on gaining an insight into to complexities and challenges involved in implementing an EHR system, taking the current South African situation into consideration. The research study constitutes a multi-disciplinary literature review and a limited in scope and extent narrative enquiry. The purpose of the latter being an attempt to validate some of the insights gained from the literature. The value of the research study stems from the fact that an EHR system will form an essential component of the NHI initiatives supporting infrastructure and the insights gained from the research study could inform the project's management strategy.