|The purpose of this study was to conduct an exploration of the potential impact of the supervisory relationship on the development of cognitive complexity of master’s students in a counseling practicum course. A priori themes of self/other awareness, motivation, autonomy, and epistemological cues were used as indicators of the presence of developing cognitions. The study was qualitative in nature. Four cases were intensively studied throughout the fall semester at a southeastern, public university. Two of the cases were bounded by the supervisor-supervisee pair; whereas, the other two cases included only the perspectives of the supervisees. The supervisors were second or third year doctoral students enrolled in a counseling supervision course. The supervisees were master’s students enrolled in either a School Counseling or Clinical Mental Health Counseling clinical practicum. Data were collected digitally through electronic interviews via Dropbox cloud storage service. Individual case summaries and a cross-case analysis enabled various themes to emerge that seemed to influence the development of cognitive complexity within the supervisor relationship. The impact of the supervisory relationship, the nature by which feedback was provided, the types and timing of intervention strategies used, and the appropriate awareness and response to the supervisee’s developmental needs were emergent themes indicative of the supervisory relationship’s influence on the supervisees’ development.