The importance of career counseling within our educational and professional systems is clearly recognized, yet little attention has been directed toward explicating the career counseling supervision process. Research on personal–emotional counseling supervision has stressed the critical importance of the supervisory relationship. The purpose of this study was to better understand the nature and effect of the supervisory working alliance in the supervision of career counselors, using case study methodology. Results point to the importance of explicitly addressing the working alliance early in the work, exploration of affect in supervision, and cognizance of the power differential inherent in a training relationship.