This chapter defines privilege and discusses how it can manifest in students classrooms, and it then outlines how mindful listening can offer critical ways to understand and dismantle privilege. Privilege signals belonging in a dominant group, but paradoxically, it also disconnects us from one another and from a holistic identity. The most common reactions are described as resistance that comes from members of dominant groups who presumably do not want to acknowledge their privilege. The mindfulness skill of deep listening allows us to better understand and interrupt our own privilege by preventing many of the defensive reactions that keep privilege intact. Privilege describes the ways that systems of oppression have been built to advance the lives of dominant groups while placing numerous barriers in the way of members of marginalized groups. Each form of oppression has its flip side of privilege: male privilege, heterosexual privilege, able-bodied privilege, class privilege, and race privilege.