Digital transformation is reshaping African economies, yet a noticeable divide exists between Anglophone and Francophone countries regarding cybersecurity and digital maturity. This paper examines how cultural, legal, and historical legacies influence these differing trajectories. Drawing on theories of colonial legacy, cultural capital, and innovation systems, a mixed-methods approach—including qualitative case studies and quantitative comparisons—highlights differences in regulatory frameworks, private sector engagement, and educational infrastructures. The findings suggest that anglophone countries’ adaptable legal systems, robust international partnerships, and access to English-dominant digital resources offer distinct advantages over their francophone counterparts. Implications for policy reform and harmonizing digital strategies across the continent are discussed.