Based on a cross-national study conducted in Northern Ireland, England, and the United States, this article expands current literature by examining 4 teacher educators' efforts to prepare preservice teachers to teach controversial issues. Teaching controversial issues, strongly advocated for decades, is both urgent and risky, especially in divided societies. The risks include emotional reactions that interfere with learning, inflammatory discourse threatening to students, and criticism from community members or school administrators. Using vignettes from class sessions and interview data, this article highlights strategies teacher educators taught their students to deal with these risks, as well as the approaches they used to teach them. Overall, the teacher educators prepared preservice teachers for "contained risk-taking" when teaching controversial issues, and they enacted this stance in their own practice. The findings raise important questions, such as what balance should be struck between an open classroom climate and safe space in politically turbulent times and divided societies.