The Iliff School of Theology established a justice and peace concentration within its curriculum to respond to the challenges of racism, class and economic exploitation, sexism, and militarism by fostering social analysis and attending to the contributions of religious thought and resources to the struggles of social change. Within an institution and with a student body who both tend to be relatively privileged in terms of class and racial or ethnic background, one of the persistent issues in teaching justice and peace studies has been addressing the emergence of guilt, anger, and despair as course content challenges students (and faculty) to relinquish self-understandings, historical understandings of their religious tradition and national context, and inadequate theological and faith formation shaped by dominant narratives that ignore social realities of oppression. This pedagogical challenge has encouraged multiple professors to develop unique pedagogical approaches to educating students about justice issues in this context. This paper will draw on the insights of these approaches, in conversation with literature-based analysis, to describe the temptations students experience when learning about justice and peace in contexts of privilege. This paper also describes the pedagogical practices that emerged in this particular context, and the failures and limitations of these practices for individual and institutional transformation.