The persistently high youth unemployment rate has long been one of the most pressing socio-economic problems in South Africa. This calls for a mix of innovative, creativity, digital skills, and entrepreneurial spirit to create job opportunities and prepare the youth for the digital economy. Digital entrepreneurship is perceived as a key pillar for job creation and economic growth. The purpose of this chapter was to investigate the role of digital entrepreneurship development in promoting youth employment through the application of novel digital technologies and the innovative application of such technologies. Barriers to effective digital entrepreneurship development were identified and among others include inadequate funding, lack of infrastructure and resources, lack of digital and entrepreneurial skills, poor collaboration between stakeholders, lack of awareness in digital entrepreneurship opportunities, and lack of appropriate mentors and role models. The chapter proposed a roadmap for promoting digital entrepreneurship development among youth in South Africa.