This article explores the underlying and epiphenomenal manifestations of milieus and contexts that serve to control and undermine, or provide pathways to, the discussion of controversial issues in classrooms. Given the importance of teaching and discussing controversial issues, as an essential lever for democratic citizenship education, I draw on two empirical case studies in Korea and Latvia. These cases suggest a variety of implications for teacher education programs and education policy makers, both domestically and abroad, including the need for teachers to develop a clear rationale for teaching controversial issues; understand their role as mediator of the larger normative mandate of citizenship education in their school and the reality of their particular context; and reflect upon their pivotal role as curricularist, gatekeeper, and professional within context and, in some cases, change the epistemological cultures of their classrooms and schools to foster free expression of ideas within an open and inviting classroom climate.