This study examined the experience of a first-year teacher's encounter with Confederate heritage while teaching about slavery and its legacy in a nearly all-white rural high school in a southern state. Data was collected in four interviews over the course of one academic year and through the participant's journaling of critical incidents in her classroom. Data was analyzed through a series of open and pattern coding. The teacher, identifying as a white suburban-raised Northern, adopted the framework of multiple perspectives to foster students' understandings about the harmfulness of Confederate symbols. Yet, the participant felt disillusioned and, at times, ineffective due to her limited experience in Neo-Confederate spaces, tensions between her white identity and teaching about race, her students' academic disinterest, and a lack of subject-specific mentoring. Findings demonstrate the presence of context-specific impediments, or hard contexts, that make the task of teaching hard history even more difficult in some settings and posit limitations of a multiple perspectives framework on issues of racial justice.