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This study examines how two students, Daphne, who self-identifies as White, and Milagros, who self-identifies as AftoLatina, experience critical self-reflection coursework in one preservice undergraduate education course in a small, liberal arts college in the Mid-Atlantic. Findings suggest that while White preservice teachers may find course assignments that prompt critical self-reflection challenging because they elicit self-examination of often unconscious sources of privilege, preservice teachers of Color may find the same assignments challenging because they invite recollection of potentially painful aspects of lived experience with societal inequities. The paper concludes with a discussion of the responsibility preservice education programs have to better differentiate both the process and expected product of critical self-reflection to mitigate harm and maximize benefits for all students.