This chapter illuminates critical moments that have characterized Kenya's media landscape from the pre and post colonial period. In focus is the media landscape's movement from a checkered press history, to an ever-expanding digital media ecology. Just like other international media environments, Kenya's media landscape has experienced varied disruptions, necessitating the need for continued introspection about how to remain relevant and innovative. Kenya's media landscape operates under a blend of liberal, authoritarian and communitarian ideologies, which has presented several challenges, but also opportunities. Challenges include longstanding concerns about political ownership, commercialization and over-regulation. Opportunities include the rise of investigative journalism and other forms of niche reporting such as science and environmental journalism. Newer journalism models such as constructive journalism are gaining ground, and an active civil society plays the watchdog role of holding power accountable. The chapter concludes by illuminating important scholarly texts that present more knowledge about Kenya's media context.