In classrooms, race-based bias, discrimination, and inequities result in unsafe and unproductive learning environments. Teacher educators are charged with helping preservice teachers develop racial literacy skills. This self-study explores the ways in which two White teacher educators recognize and attempt to manage challenges during field instruction of White teacher candidates. The teacher educator researchers explore their own Whiteness and use a racial lens to critique their practices. Post-lesson-debriefing conferences between teacher educators and their candidates are shared as illustrative vignettes to reveal instructors' teaching challenges and failures. Implications for working with White teacher candidates, improvements to field instruction practices, student teaching curricula revisions, and programmatic changes are posited.