Dialogue about social and political conflicts is a key element of democratic citizenship education that is frequently advocated in scholarship but rarely fully implemented, especially in classrooms populated by ethnically and economically heterogeneous students. Qualitative case studies describe the contrasting ways 2 primary and 2 middle-grade teachers in urban Canadian public schools infused conflict dialogue pedagogies into their implemented curricula. These lessons, introducing conflict communication skills and/or content knowledge embodying conflicting viewpoints as learning opportunities, actively engaged a wide range of students. At the same time, even these purposively selected teachers did "not" often facilitate sustained, inclusive, critical, and imaginative exchange or deliberation about heartfelt disagreements, nor did they probe the diversity and equity questions surrounding these issues. The case studies illustrate a democratic education dilemma: Even in the classrooms of skilled and committed teachers, opportunities for recognition of contrasting perspectives and discussion of social conflicts may not necessarily develop into sustained democratic dialogue nor interrupt prevailing patterns of disengagement and inequity.