Increased access to Internet technologies in Kenya has caused political communication in digital media spaces such as Twitter and Facebook to thrive. It has also led to the emergence of political influencers who shape political conversations in various ways. While these individuals are celebrated by some, they have often faced government repression, arrests, threats and forced disappearances. The overriding reasons given by the government to justify such a repression have always been to curb malicious dissemination of messages that is a threat to national security. While their role in public conversations has always been contentious – dissident for some and whistle-blowers for others – their role in shaping public conversations cannot be ignored. Contextualising their work in Kenya's mediated environment, this study investigates how two prominent bloggers/influencers employ social media to disrupt, expose, and resist authoritarianism in Kenya. By examining the online activities of two bloggers – Robert Alai and Cyprian Nyakundi – I illustrate the larger dynamics of online activism in Kenya and how online activities can lead to different political outcomes and lead to an understanding of the different forms of anti-authoritarian resistance taking place in postcolonial Kenya.