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The emotional aspects of principals’ work continue to expand, even though the topic has been historically overlooked in the literature and legislation that defines school leadership roles and responsibilities. This study uses findings from interviews with 13 secondary school principals to map the emotional terrain of the principalship by identifying conditions in their daily work that incite emotion-generating situations. Participating principals identified five workplace conditions that generate emotional responses, including advocating for students, work intensification, navigating their local policy context, working with individuals who are angry or upset and managing crises or tragedies. The findings suggest a need to acknowledge the heavy emotional burden associated with contemporary school leadership, and to clarify legislated expectations and responsibilities placed on school principals.