Turkish democrats, scholarly community, and even Western policy circles once had high hopes from the alleged moderation and democratization of Islamist social actors in Turkey. The current democratic breakdown in Turkey, occurring mostly with the collaboration of Islamic social actors, posits a huge puzzle in this sense. What did go wrong? In this paper, I focus on the Islamic trade union of Turkey, which was one of the first Islamic civil society actors to embrace liberal democratic discourse during 1990s. Having more than 400,000 members, HAK-IS is the representative of Islamic social movement within the organized labour of Turkey. During 1990s, HAK-IS was a vivid supporter of democratic values in Turkey; in fact, it was even more enthusiastic than leftist and centrist trade unions in its support for membership of Turkey to European Union. Thus, scholars saw HAK-IS as the leader of transformation of Islamists into democratic civil society organizations. During the rule of the Justice and Development Party, however, HAK-IS has turned into a loyal supporter of JDP. It constantly supported all political positions of JDP, even when these positions were clearly undemocratic. Were scholars wrong in their praise of HAK-IS as a democratic organization? Or, did HAK-IS lose that capacity in time? Solving this puzzle of HAK-IS, I believe, can help us understanding the Islamic social movement’s democratic journey in Turkey. This paper relies on interviews with old and current HAK-IS managers and an analysis of all magazines published by HAK-IS from 1986 to 2013. Relying on the original data, I argue that “democratic transformation” of HAK-IS in 1990s was only limited to strategic cooperation with several liberal trade unionists coming from a leftist past. The bureaucratic structure of HAK-IS, however, stayed the same. While HAK-IS managers with an Islamist past benefited from the human capital of liberal trade unionists, rewarding them with high-level posts in the trade union, they actually never allowed these liberal-minded trade unionists to grasp real power in the union. Once liberals of Turkey experienced an ideological and political break with the JDP government around 2013, liberal-minded trade unionists of HAK-IS were removed from HAK-IS as well. Thus, I argue, the case of HAK-IS teaches us a crucial lesson. The survival of bureaucratic structures within organizations prevents a true democratic transformation process. Scholars must be careful to distinguish strategic rhetorical moves of institutions from real organizational transformations.