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This paper examines the emotional labor and professional courage of assessment practitioners who champion diversity, equity, and inclusion (DEI) in politically charged and change-resistant higher education environments. Far from being neutral, these assessment professionals act as “tempered radicals” (Meyerson & Scully, 1995)—individuals who navigate institutional norms while advocating for transformative equity work. Using tempered radicals and theories of “small wins”, this qualitative study explores how assessment professionals manage emotional and professional tensions, maintain resilience, and persist in their advocacy despite fear, isolation, or backlash. Through this lens, the paper illuminates the often-invisible emotional work required to challenge systemic inequities, positioning these practitioners as moral agents committed to justice, empathy, and student-centered transformation within institutions that often resist such change.