Background/Context: Research indicates that across democratic societies, teachers face numerous intellectual and emotional challenges when handling controversial topics in the classroom. Less attention, however, has been paid to how teachers' willingness to teach controversial topics intersects with political and other societal factors in different sociopolitical milieu and, in particular, in an authoritarian-democratic and culturally diverse state like Singapore. Focus of Study: This study focused on constraints to the teaching of controversial topics relating to diversity and the manner in which teachers navigated their personal beliefs amidst the evolving contours of public and official discourses in Singapore. By attending to the intersections of teachers' beliefs, state policies, and other sociopolitical factors, we aimed to inform scholarship on the teaching of controversial topics and illuminate states' powers to demarcate the discursive spaces of teachers. Research Design: The study adhered to the qualitative case study design. We collected data from interviews that featured various elicitation tasks to describe 35 social studies teachers' perceptions and practice of controversial issues discussions relating to topics of diversity. Additionally, we drew on policy and curricular documents to portray the evolving contours of public discourse in Singapore. Findings/Results: The findings highlight how the participants, influenced largely by state policies, differentiated between topics that were controversial-appropriate and controversial-taboo. In spite of the numerous legal constraints limiting the nature of public discussion of race and politics, the majority of the teachers regarded these topics as controversial-appropriate. There was, conversely, a consensus among the participants that topics related to sexual orientation were controversial-taboo even though there were no similar laws constraining public discussion of this issue. Conclusions/Recommendations: This study challenges conventional assumptions about the impact that state-imposed constraints and controls have on the teaching of controversial topics in schools. Under some circumstances, state controls and constraints can result in teachers having more freedom to discuss controversial topics because of the clearly demarcated political and social boundaries. However, if the state's position is ambiguous, this may result in a Kafkaesque situation in which teachers become even more conservative in their curriculum decision making due to a heightened sense of uncertainty and insecurity. Ultimately, the study brings to light the nuanced ways that state control and censorship influence the spaces and limits of issues-centered discussion, and underlines the need for research that attends to various social forces that frame the teaching of controversial topics in different democratic settings.