Since 2011, the New York City (NYC) Department of Education (DOE) has engaged in a campaign to increase the number of bilingual programs it offers. This case presents the experiences of a principal who was asked by her superintendent to open a new Dual Language program. Having been a principal for only 1 year, and with little expertise about English Language Learner compliance and instruction, the principal engaged in a learning process that illuminated significant complexities not just about bilingual education policy, but also about the DOE's bureaucracy, policy implementation in NYC, and the ambiguity of the principalship.