Using technological applications, smart construction aims to improve the planning, management, and execution of construction project delivery. This has the potential to forestall several of the challenges associated with project execution and delivery using conventional methods. Therefore, this study evaluates the challenges of implementing smart construction sites in the South African construction industry. Employing a quantitative technique, data was elicited from the target respondents who were sampled using convenience and snowball sampling techniques. Retrieved data was analysed using exploratory factor analysis using the principal component analysis extraction technique. The study’s findings showed that the significant challenges faced by implementing smart construction sites in South Africa are institutional drawbacks, financial impediments, and lack of technical expertise. The study contributes theoretically and practically to the growing call for construction digitalisation as it fills the gap in knowledge by unravelling the encumbrances of the use of smart construction sites. Furthermore, the study’s outcome is a sound theoretical base for future studies geared towards construction digitalisation in developing countries.