South African government has since 1995, developed a considerable body of legislation that defines a holistic Human Resource Development Framework for the Private Security Sub-sector. Through this legislation development process, the Private Security Sub-sector has made considerable progress in implementing this body of legislation. However, in spite of this achievement, policy implementation success indicators are not commensurate to the policy development success indicators and several challenges are still impeding skills development of workers. In particular, the Private Security Industry has moved steadily beyond the systems development phase. It has made strong progress in implementing stipulations of the skill development legislation in the sector with the support of the skills levy fund as well as donor support. Considerable attention has been paid to the implementation of the different types of skills development related legislation including funding the skills development initiatives and employment equity. The cases examined in the study reflect varying and different degrees of success in achieving set targets as well as challenges that have emerged in the implementation process. There is an indication that the dire shortage of skills in the private security subsector persists and the efforts of the drivers of training and development in the sector, the Safety and Security Sector Education and Training (SASSETA), the Private Security Industry Regulatory Authority (PSIRA) and employers have made little impact on this need. This state of affairs cannot be allowed to continue indefinitely. The study revealed a range of critical National Skills Development Strategy targets that have not been met throughout the period under study. For instance employers have failed to meet obligatory targets of employing training employees to achieve at least ABET level 4. In addition, only 54% women have been trained and 4% people with disabilities. Furthermore, there are a number of other training obligations that compounds the challenge by infringing on the rights of the affected groups. This also retards the social and economic development of workers as well as that of the country. South Africa continues to lack effective, robust crime fighting groups of skilled crime fighters in spite of the training levy funds that have been spent on skilling the Private Security Sub-sector. The point of departure of this study is that the Skills Development initiative is a sector programme which must be led by the sector itself, especially the employers. The employers in the workplace constitute a valuable source of capacity to effectively implement the skills development legislation. SASSETA and PSIRA are the promoters and drivers of the participation of Private Security Service providers in skills development in pursuit of the 2014 vision. It is imperative that SASSETA and PSIRA, as proponents and catalysts of skills development, listen to the concerns raised by employers and continuously engage them as well as the intended beneficiaries, the workers. The research revealed that benefits of the skills development legislation will only be realised when critical elements such as prioritising the identified challenges and shortcomings are the focus. The study highlighted the need for industries to capacitate their employees to understand the intended benefits of training regulations and requirements. Developing management and leadership capacity, creating conditions that are conducive for skills development at the workplace, and building the capacity of Small, Medium and Micro Enterprises (SMMEs) through innovation and support were also identified as critical for successful implementation of policy in this regard. The need to train and capacitate leaders in corporate governance and financial management was also among the findings identified by the study. The findings will present an opportunity for scholars and researchers to debate and argue their merits and demerits which will in turn influence policy-making processes positively.