School leadership is required to navigate difficult issues concerning the religious liberties of their students. December is a month filled with secular and religious holidays. It is the one month on the school calendar filled with joyous cultural celebrations. However, it can also become a quandary for leadership when attempting to balance the religious and cultural diversity of American school students. The Supreme Court of our land has historically ruled for the separation of religion and the state. Therefore, school leadership has the task of guiding schools and educators to not violate intentionally or accidently the religious liberty of all students. This paper specifically addresses the "December Dilemma", examining relevant court cases, one specific local "dilemma", and the results of a survey conducted of school district administrators and classroom teachers. The overall recommendation is that school district leaders should consider school district policy that not only protects the student, but the school district itself.