Western scholars have previously predicted Weibo and social media will provide Chinese netizens with an opportunity to foster its nascent civil society. However, the growing applications of surveillance technologies have challenged this rosy, yet deterministic prediction. This chapter argues that Jürgen Habermas's concept of public sphere is less likely to function properly, given the pervasive applications of surveillance technologies in China, which has fundamentally challenge its many assumptions. Using Habermas's analytical framework that is used to better comprehend the role of social media in Chinese politics, the authors argue that information technologies turn out to deteriorate the formation and maintenance of a public sphere for Chinese civil society. The authors employ a case study to examine the interrelations among social media, surveillance technologies, civil society, state power, economic development, political process, and democratization in China as demonstrated in Hong Kong's Anti-Extradition Law Protests.