As Cornell West (1994) aptly determined, Race Matters. Although the origins and accuracy of what American society believes to be race is complicated, it is no less a prevalent force in human interaction and conflicts therein (Berry, 2013). As an educator, the contrast of my perceived racial and cultural identity has been the source of considerable attention inside my classroom. As a member of the majority or White population, at times it may appear I have been established in opposition to the minority and predominately Black students by the prevailing status quo (Helms, 1993). The growing research in the educational field continues to reinforce the conundrum of racial identity, especially between White teachers and students of color. What manner of predisposition is therefore to be expected when a teacher transitions to the role of a school volunteer tasked with engaging Black students outside of the classroom using restorative practices? This autoethnographic study serves to explore that phenomenon.Utilizing Racial Identity Development theory as a framework, this study will draw upon the established credence of racial identity development with respect to the social construct of race and how it functions in the dynamic of a non-educator, White, adult, male working with Black students. My identity and the perception of its impact will be examined critically, in an attempt to expose any new knowledge that informs successes and challenges that I personally encountered engaging Black students in a restorative manner. Thematic analysis, in accordance with a rich descriptive (Ellis, 2010) construct of autoethnography, will direct a series of interactions with the target population during the course of a semester at an urban alternative public-school setting.White teaching professionals have come under tremendous scrutiny in the last generation in regard to the racial dynamics of the classroom. As the educational field peers inward to examine the structural implications of racial identity and their association with educational outcomes (Darling-Hammond, 2010), the growing emphasis on how Whiteness (Hines III, 2017) impacts the classroom invites adjacent conversations in the space around the classroom. Additionally, the position of power a teacher holds affects this dynamic, doubling the impact a White teacher may have on these outcomes (Glimps & Ford, 2010). As a licensed public teacher with a racially diverse background, I am qualified and positioned to add to the growing field of investigation into the racial paradigms of education. However, that is not the only avenue through which I contribute. With respect to my upbringing and identity, I present a potentially unique and contrasting perspective on race in education. This is further enhanced by my desire to explore the space outside of the classroom, thereby doubling down against the two most common areas of examination in this racial renaissance of sorts in modernity;. structural White hegemony and the teacher’s position of power (Chandler-Ward & Denevi, 2022; Talusan, 2022).Combining a unique perspective with an alternative position may afford both a contrasting and complementary narrative to the growing data points of how race and the attributes of White identity are impacting educational outcomes. Utilizing an autoethnographic model of qualitative research, my hope is that this immersion experience and subsequent introspection will reveal more than something different; but by virtue of the aforementioned complement and contrast, will reveal a contributing factor of both White racial identity and educational support that will serve the continued evolution of education to encompass the diversity of backgrounds of all teachers and students without compromising the need for equality.