Educational administration is a rich domain of scholarship and practice, but one subject rarely discussed is its dark side. This study explored the question: What types of maladministration occur in schooling systems? The goal was to develop findings to inform existing prevention strategies. Focused on the Canadian context, data sources included 64 reports from disciplinary hearings of administrators in the Provinces of Ontario and British Columbia, complemented with other publicly available sources such as news stories. Findings indicated only a small minority of populations of administrators were subjected to disciplinary investigations and sanctions, but the targeted misconduct was often severe. Analysis revealed eight dimensions of maladministration, with sexual misconduct against students and financial transgressions being the most frequent. Academic dishonesty in the context of standardized testing and gendered patterns of maladministration also stood out. A typology emerged that highlighted the mai...