This paper analyzes continuities and discontinuities of collective efforts toward enhanced cyber security in Eastern Africa, with a particular focus on Kenya, Ethiopia and Somalia. Focusing on the challenges that have followed the contours of East Africa’s distinctive digital cultures, it challenges the view that cyber security and cyber resilience are simply technical problems that can be solved by reducing the gap with more technically advanced nations. On the contrary, it shows how cyber security is an inherently political challenge and that, in the absence of adequate checks and balances, the increasing securitization of domestic and international politics may require costly trade-offs with individual and collective freedoms.