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This paper focuses on three White activists (Rachel Davis DuBois, Harry G. Boyte, and Al Lingo) in the Southern Christian Leadership Conference in the late 1960s and their involvement in interracial dialogues through Operation Dialogue. Operation Dialogue’s stated aim was to engage White working class Southerners as foot soldiers in the Civil Rights movement. Drawing from Davis DuBois’ autobiographical writings, speeches by Harry G. Boyte, oral histories with Boyte family members and Al Lingo, and the extensive organizational files of SCLC, I detail the challenges of establishing interracial dialogues in the context of a Black Southern Civil Rights organization and explore how White activists’ perspectives on White privilege and anti-Black racism were influenced in the process.