Asian, Black, Indigenous, Latine, and Pacific Islander students have increased their enrollment in private schools (2012–-2020) (NCES, 2021a) and have become the majority population in American public schools (NCES, 2021b), yet many educators are not adequately prepared to teach students from diverse backgrounds (Ladson-Billings, 2017; Paris & Alim, 2017). Within the field of choral music education, preservice choral educators are mostly prepared to teach Western European classical repertoire and bel canto vocal technique, both based on a Eurocentric paradigm (Good-Perkins, 2021b). This paradigm, however, is unlikely to be appropriate for students who are versed in diverse musical cultures (Carlow, 2006; Gustafson, 2008). The resulting cultural rift between students and choral educators can lead to student exclusion, cultural assimilation, and silencing (Bradley, 2015). Culturally sustaining pedagogy (CSP) is a theoretical construct focused on cultural and linguistic plurality in the classroom. CSP can address the potential cultural rift between educators using Eurocentric teaching paradigms and students’ unique cultures and ways of knowing music, sustaining students’ cultures and thereby preventing student silencing and assimilation (Good-Perkins, 2021b). Therefore, the purpose of this study was to discover the ways, if any, in which three high school choral educators—with multiple musical-cultural proficiencies—enacted culturally sustaining pedagogy in the choral classroom and student perceptions of their teaching. To address the purpose of this study, a multiple case study research method (Stake, 2013) was used. The themes that emerged upon completion of within case and cross-case data analysis included: musical-cultural alignment, importance of cultural dexterity, code-switching, and style shifting, interstitial space between styles, and developing connections. The implications of this research pertain to proposed changes in music teacher preparation and in-service music educator professional development. These changes could positively impact the skills and interests of the future pool of music education program applicants. The potential result of such changes at the K-12 and tertiary levels could be an increase in the diversity of music educators.