This chapter examines the tripartite link between civil society, the middle class and democratisation in Thailand from the departure of semi-democracy in 1988 to the latest coup in 2014. It conceptualises Thai civil society and the Bangkok middle class as contingent authoritarians. Both social forces have the intrinsic inclination towards authoritarianism due to their institutional dependence on state sponsorship. However, in the short term, the political actions of both social forces are contingent upon the contextual settings, for the reason that they are consistent defenders of their own interests (a privileged position in the country’s political economy) and group ideologies (a morally conservative mode of governance).