There are significant inherent challenges in teaching students about structural racism resulting from white supremacist systems but overcoming these challenges leads to better outcomes. The goal may be to create a level of awareness that spurs action from the micro- to macro level. However, the means may result in further marginalizing students of color and either creating resistance in white students (who refuse to concede they have privilege) or guilt and shame in white students (who focus on their individual atonement rather than promoting structural change). This paper will discuss flaws in current theoretical and pedagogical approaches to antiracism education including first-person accounts of such errors from the experiences of the author. It will then posit how a primary focus on the history and current context of structural white supremacy in the United States may help alleviate the aforementioned failures of educating around issues of race.