Quality civic education is often understood as involving discussions of controversial social and political issues, a task made more difficult for teachers amidst the kind of political polarization that characterizes the current political climate. This study explores high school social studies teachers' thinking and sensemaking related to disclosing their personal political beliefs in the classroom in light of the challenges posed by increased contentiousness. In this article, I present data from three rounds qualitative interviews conducted in 2017, 2018, and 2019 with social studies teachers nationwide that illustrate the complicated, contextual nature of teachers' decisions about political disclosure. Teachers described varied, sometimes shifting stances toward disclosure today and identified factors that both encouraged and discouraged their willingness to share their opinions in the classroom. This study illuminates the complex, contextual nature of pedagogical decisions on disclosure and the conditions that complicate some of the assumptions in the literature.