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The notion of working from home is not a new concept. However, it has become a buzzword amidst the COVID19 pandemic. Some scholars were already engaging in the work-from-home (WFH) concept a few years before the pandemic. However, contextualization of this concept from a South African perspective only became compelling during COVID19 times, when various industries had to shift their focus and adjust rapidly. This paper aims to investigate through literature reviews, and to understand the cybersecurity challenges that emerged because of this adjustment. Moreover, to investigate South Africa’s readiness and the lessons learned from this significant shift.