Background: White school counselors comprise 77% of the school counseling workforce, yet over half of U.S. students are students of color. As student populations continue to diversify, understanding how school counselors develop culturally responsive practices is essential. Cultural humility is a protective factor in counselor–client relationship building, yet no studies exist exploring cultural humility specifically in school counseling contexts. Objectives: This study was undertaken to understand how White school counselors experience developing cultural humility in working with students of color. Research Questions/Hypotheses: How do White (majority culture) school counselors experience developing cultural humility while working with students of color? Methods: We used interpretative phenomenological analysis to gather the experiences of middle and high school counselors from the Midwestern United States. Results and Conclusions: Four themes emerged: confronting cultural dissonance and being humbled by cultural mistakes/missteps; engaging in intentional and difficult learning shaped by relationships with students, families, and colleagues of color; sustaining commitment through ongoing challenges; and meeting students of color where they are by setting aside cultural assumptions and centering student experiences. Cultural humility development is a continuous, relational, and reflexive commitment requiring vulnerability, authenticity, and integrity. We discuss implications for practicing school counselors, school counselor educators, and future research related to cultural humility in working with students of color.