Critical Discourse Analysis (CDA) has reached a certain degree of canonical status, as it is widely used and applied as a research and analytic tool. However, hitherto it has been taken for granted that CDA can be applied and practised anywhere unproblematically. There is still a dearth of scholarly attention that focuses on the tensions and in/compatibility of CDA as a critical and analytical toolkit when applied in authoritarian regimes. This article attempts to fill the gap of research in this field by relocating the practice of CDA to the Singaporean context--a context widely known for its conservative political culture where dissent sits uncomfortably in its political arena. Although CDA can be valuable for research in such a context, the consequence of applying such a "critical" toolkit may result in more than the generation of academic knowledge. I argue in the paper that doing CDA in an authoritarian context may be a risky enterprise. Thus, strategies and modes of expression must be adapted for the kind of critical work that CDA does. The paper concludes by suggesting "academic activism" as a possible way for working around the risky terrain of doing CDA in Singapore.