The global construction industry has long been slow to adopt emerging technologies, and the South African construction industry is no exception. Among the technological innovations gaining prominence, wearable technologies have demonstrated significant potential to enhance health and safety management on construction sites, particularly in the wake of the COVID-19 pandemic. Despite their benefits, the integration of wearable technologies in the South African construction industry remains limited, largely due to a variety of persistent challenges. This study investigates the challenges hindering the adoption of wearable technology on construction sites in South Africa, particularly in the post-COVID-19 era. A quantitative, descriptive survey was conducted among construction professionals in the Gauteng Province, chosen for its high concentration of professionals and diverse construction activities. Data was collected through structured questionnaires administered to purposively selected respondents, yielding 52 valid responses from 60 distributed questionnaires. Analysis involved the use of Mean Item Score (MIS), Standard Deviation, and One-Sample t-test, with a significance benchmark of 3.5. Instrument reliability was confirmed with a Cronbach’s alpha of 0.712. Findings revealed that all identified challenges were statistically significant (p < 0.05), with the most critical being High cost, uncertainty about return on investment, lack of critical information, resistance to change, and limited technical support. Addressing these challenges through policy support, training, and awareness programs is vital to unlocking the benefits of wearable technology for safer construction environments in South Africa. The study provides valuable insights into the challenges to wearable technology adoption in South African construction, offering a foundation for future research and policy interventions.