Despite the recognised benefits of digitalising construction processes, government organisations in South Africa continue to face persistent obstacles in implementing digital procurement systems. This study evaluates the major challenges hindering the digital transformation of procurement in government-funded construction projects, with Gauteng Province serving as the case study area. A quantitative research design was employed, using a structured questionnaire administered to seventy-six construction professionals involved in public sector projects. Descriptive and inferential statistical techniques were applied to analyse the responses. Findings highlight critical barriers, including concerns about data security and vulnerability to cyberattacks, a shortage of digitally skilled personnel, frequent system malfunctions, and risks associated with asset management and competition. Additional challenges identified relate to policy inefficiencies, organisational resistance to change, and inadequate awareness of digital procurement benefits. The study contributes novel insights by consolidating context-specific barriers to digital procurement in the South African public sector, an area underexplored in current literature. Limitations stem from the study’s focus on a single province and a modest sample size, suggesting the need for broader studies across multiple regions. Practically, the findings provide guidance for policymakers and public organisations to strengthen institutional frameworks, invest in digital skills training, and enhance data security protocols to enable successful digital transformation. Socially, the study emphasises the potential for digital procurement to promote transparency, reduce corruption, and improve efficiency in public sector construction projects, thereby advancing sustainable development in South Africa’s built environment.