One way to support aspiring and current administrators is through the use of case study teaching (Barnes, Christensen, & Hansen, 1994). Using case studies as a teaching and learning tool helps bring real-life situations into principal preparation and support programs. Case study approaches provide students with time to interrogate contemporary issues, reflect on their own practices and understandings, and debate possible responses to the issues. Using case studies as a teaching tool is not new (Llewellyn, 1930; Weaver, 1991). Over the years, they have been utilized in business, law, and education, among other disciplines. What is unique about case studies is that they can be generated to reflect the contexts in which people are currently working. This special issue focuses on case studies specifically for educational administrators and leaders in Canadian contexts. While Canadian education systems are similar to many Western countries such as the United States, England, and Australia, they also have their own unique policies, traditions, and nuances that set them apart from others. The 10 case studies showcased in this issue are intended to act as a springboard for practicing and aspiring principals to reflect upon, and work through some of the current challenges they encounter in Canadian schools.