Supportive relationships with counselor educators as dissertation chairs are valuable to doctoral students overcoming barriers to successful completion of their dissertations. Yet, few have examined the complex and mutually influenced dissertation-chairing relationships from the perspective of dissertation chairs. Using hermeneutic phenomenology, we interviewed counselor educators (N = 15) to identify how they experienced dissertation-chairing relationship dynamics with doctoral students. Counselor educators experienced relationships characterized by expansive connections, growth in student autonomy, authenticity, safety and trust, and adaptation to student needs. They viewed chairing relationships as fluid and noncompartmentalized, which cultivated mutual learning and existential fulfillment. Our findings provide counselor educators with examples of how empathy and encouragement may help doctoral students overcome insecurities and how authentic and honest conversations may help doctoral students overcome roadblocks. Counselor education programs can apply these findings by building structures to help facilitate safe and trusting relationships between doctoral students and counselor educators.