Unlike the millennials from the industrialised world who were raised amidst an increasingly online and socially networked society, their South African counterparts at previously disadvantaged universities have some weaknesses similar to those of digital migrants. These weaknesses are caused by the limited exposure millennials in South Africa have to digital devices and Internet connectivity. In spite of these impediments, their future careers in an increasingly globalised world require them to behave like, transact and engage with full-fledged digital citizens from the global north. Digital citizenship is the ability to use technology safely, responsibly, critically, productively and civically. This raises intellectual curiosity about the extent to which the African millennial is prepared for a world that expects them to be digital citizens. This article, therefore, investigates the challenges faced by the South African millennial as they navigate an unusual route to digital citizenship. We adopted the activity theory for a mixed-methods study that consists of a survey of 148 questionnaires and 15 in-depth interviews. The findings show that while university-going millennials acquire digital literacy, their development of digital citizenship is affected by lack of mentors and access (i.e. connectivity and devices) at home and lack of soft skills training (i.e. online safety, digital etiquette and inadequate information literacy) at the university.