Twenty years after the 1997 political changeover in Hong Kong, the “one country, two systems” arrangement is facing serious challenge. Many in the Special Administrative Region see Beijing as an unwelcome control master; calls for self-determination have gained popular support. Even a segment of the economic elite in Hong Kong feel sidelined enough by Beijing’s appointed chief executive in the territory to ask for his ousting, indicating failure of Beijing’s long-cherished “united front” strategy of co-optation. News media self-censor themselves under increased political pressure, but frontline journalists and independent media are fighting on. Against this background and the preceding major political events, this chapter reviews the development of independent media as voices of dissent in post-1997 Hong Kong. It examines the spectrum of political positions involved, and explores their implications on real-life politics. It sources from Chinese and English journalistic and academic studies, and references media programs as well as social media content on the Internet. China’s interpretation of the Basic Law, proposal of localization of Basic Law’s Article 23 in Hong Kong, the moral and national education curriculum, and the electoral reform blueprint are some of the major events touched upon.