Clinical supervision is a cornerstone of clinical training, and supervision experiences are associated with important outcomes (e.g., stronger working alliances and more trainee disclosures in supervision). Psychology has made strides in understanding how cultural processes unfold in supervision, with the multicultural orientation (MCO) model garnering increasing empirical support, but less is known about the dynamics that occur based on racial differences between supervisees and supervisors. Therefore, within cross-racial supervisory relationships, we examined the associations between cultural humility, cultural comfort, and supervisees’ satisfaction with supervision, disclosure in supervision, and the supervisory working alliance. Survey results from Black, Indigenous, and people of Color (BIPOC) trainees ( N = 116) receiving supervision from White supervisors indicated that supervisees who rated their supervisors high in cultural humility and cultural comfort also reported higher supervision satisfaction and a stronger supervisory working alliance. Perceptions of supervisors’ cultural humility, but not cultural comfort, were related to a higher willingness to disclose in supervision.