Multiple and complex issues simultaneously present themselves for the principal's attention. Learning how to identify, prioritize, synthesize, and act in relation to these issues poses a particular challenge to early career principals. This case study engages aspiring and current school leaders in critical reflection upon leadership opportunities and practices in a simulated setting that elicits challenges commonly experienced by early career principals. Discussion questions integrate educational leadership research specific to the case issues. Activity suggestions focus on use of the case as a collaborative assessment in an educational leadership admissions process, midpoint review, or course; as a self-assessment; and in supervision of principals.