This case study provides a summary of a district leader's dilemma on how to approach a number of gender identity issues that are raised within the first few months of his new superintendency. It identifies the various facets of policy and practice that need to be addressed in light of gender no longer being considered as a simple binary choice. Then discussed is how school administrators work with a variety of constituent groups to navigate implementing the necessary changes to policy and practices. Teaching notes and suggested class activities are included.