Background: Community-based youth mentoring programs are popular interventions that serve a large number of Black youths throughout the country. Interestingly, the majority of mentors who volunteer their time for mentoring organizations identify as non-Hispanic White. This study examines how White mentors address topics acknowledging ethnic/racial identity and issues centered around social justice and recognize their own privileges when mentoring Black youth in community-based youth mentoring programs. Objective: The aims of the current study were to examine: (1) whether and how White volunteer mentors address ethnic/racial identity, racial socialization, and oppression in the mentoring relationship and (2) how White mentors' awareness of their own positionality and privilege impacted how they addressed ethnic/racial identity, racial socialization, and oppression in the mentoring relationship with Black youth. Method: Utilizing a constructivist grounded theory approach, in-depth semi-structured interviews were conducted with 26 current and former mentors from six different Big Brothers Big Sisters community-based mentoring programs across the United States. Results: Findings reveal that some mentors felt uncomfortable discussing issues centered around race and others do not think it is relevant at all. Further, findings demonstrated that mentoring Black youth significantly impacts mentors' perceived awareness of social issues and acknowledgment of privileges they hold. Conclusions: Current findings highlight the need for youth mentoring programs to provide training and resources to help White mentors discuss implications of race and broader social justice issues with the Black youth they mentor.