Alongside a consolidated liberal democracy and dynamic civil society, Taiwan boasts one of Asia’s most liberal and competitive media environments. However, the pressures of intense commercial competition have created issues around professional ethics and the effects of sensationalism. Long-standing regulatory and ownership issues remain unresolved, including political partisanship across the media-sphere. Like their counterparts in other democracies, Taiwanese media companies are grappling with the transition to digital and the challenge it represents to traditional business models in a highly media-saturated society. Mediatised political spectacles, hypermedia political campaigns and communicative abundance are inescapable features of Taiwanese life. Taiwanese citizens are by many standards engaged and politically active. Yet for all the openness that goes with trailing TV cameras and politicians’ status updates on social media, the media and political communications environments in Taiwan are a cause for concern in terms of the “quality” of their contribution to Taiwanese democracy. This chapter outlines the evolution of the media system as it has experienced two waves of reform and comments on the prospects for further needed reforms within a context where digital media is challenging traditional media operations and the People’s Republic of China (PRC) casts a shadow over media freedoms.