Digital diplomacy is an important dimension in the contemporary foreign policy despite of its reliance on other factors associated with technology and political context. This article examines determinants of digital diplomacy that shape Kenya’s foreign policy. It emphasizes on internet connectivity and political leadership. Internet access is critical for digital tools and spaces to be functional. Disruptions to the internet supply or interference of the cables exposes digital diplomacy vulnerability to external shocks. Stable internet is important for successful diplomatic engagement. Since digital diplomacy is supported through digital spaces and other enablers, internet connectivity is essential. Political leadership is also important for successful use of digital diplomacy. Digital spaces vary in use and all contribute in a way to the success or failure in the use of digital diplomacy. Social media sites are highly used for digital engagements, underscoring the centrality of public diplomacy in Kenya’s foreign policy. Digital diplomacy is shaped by several factors aligned to knowledge on technology, political environment and technological infrastructure. Kenya’s successful influence in global affairs can be felt through strengthened partnerships, capacity building and robust investment on digital infrastructure.