South Africa’s private security industry is experiencing a profound transformation driven by digital disruption and the implementation of emerging technologies. Using documentary analysis, this article examines how innovations such as artificial intelligence (AI), drones, Internet of Things (IoT) sensors, biometric authentication, and cybersecurity systems are transforming the delivery of security services. Although these technologies enable predictive analytics, real-time threat detection, and automated incident response, they also present complex challenges related to privacy, regulation, and skills and workforce deficits. This article draws on socio-technical systems theory and surveillance studies. The study examines the crossroads of technological adoption with governance, regulations, ethics, and social equity. It also employs qualitative content analysis of academic literature, government reports, and industry publications to identify key trends, benefits, and limitations. This approach helps achieve the aim by demonstrating how AI and related technologies impact security service delivery, while also identifying the regulatory, ethical, and skills factors that influence their effective use. The findings reveal significant gaps in regulatory frameworks, particularly the outdated provisions of the Private Security Industry Regulation Act 56 of 2002 (PSIRA Act 56 of 2002) and highlight the need for inclusive training programmes to address digital competency deficits among security personnel. The recommendations include legal reform and more empirical studies on the effectiveness of upskilling workforce development. This research contributes to a deeper understanding of the evolving role and use of digital technologies among security service providers in South Africa and provides policy-relevant insights for ensuring the ethical and equitable integration and regulation of digital technologies within the sector.