Among the challenges faced by educators in promoting critical thinking is that of cultural compatibility. Using Singapore as an illustrative case study, this paper explores the cultural challenges and recommended strategies for the teaching of critical thinking in schools. The research for this study is based on a theoretical framework that focuses on two dominant practices of critical thinking: confrontational and individualistic on the one hand, and collegial and communal on the other. Research data shows that the main cultural challenges are the social expectations of teachers as knowledge transmitters and a perception that critical thinking is essentially adversarial. The recommended strategies are the utilisation of cooperative learning strategies and the provision of a safe learning environment. There are two major implications arising from this research study. The first is a need for policymakers and educators to be cognisant of cultural constraints in the teaching of critical thinking. The second is the significance of teacher efficacy to engender student engagement and successful learning within socio-cultural constraints. The Singapore experience adds to the existing literature by highlighting the existence and significance of communitarian practices of critical thinking in an Asian context.