Previous studies suggest that the majority of school psychologists do not believe they receive sufficient supervision, despite a growing body of research providing empirical support for supervision to maintain and improve skills. This study explores the dynamics underlying the challenges of providing adequate supervision to school psychologists. Findings suggest that supervision of school psychologists is characterized by challenges that extend beyond the traditional demarcations of clinical and administrative supervision typical in clinical settings. Supervisors of school psychologists encounter systemic challenges, unique to school settings, which must be addressed for their supervisees to be able to function successfully. The findings suggest that a clinical–administrative–systemic model of supervision is most appropriate in the supervision of school psychologists.