Over the past decade, research into principals' work intensification has revealed that principals spend significant work hours on student discipline and attendance issues, and that they report high levels of emotionally draining situations. In the current study, we examined the relationship between student discipline issues and principals' emotionally draining situations to determine if variables related to student discipline issues affected principals' experiences of emotionally draining situations. Using a correlational research design with hierarchical regression, we analysed data from a digital survey of school principals in Ontario, Canada. A total of 1434 surveys were included in the final analysis, with respondents from elementary, high-school and combined schools. Results showed a correlation between student discipline and attendance issues and principals' experiences of emotionally draining situations, while also showing that student discipline and student and parent mental health were strong predictors of principals' experiences of emotionally draining situations. These findings have important implications in supporting principals: These insights can inform principal preparation programmes by showing the need for increased training on identifying and treating emotionally draining situations. Insights may also encourage policymakers to review student discipline and student/parent mental health policies in light of the revelation of their impact on principals' work.