The core challenge is this--a difficult ethical decision, where values are in play and both sides have powerful moral arguments in their favor. One case presented in this article outlines a dilemma faced by one teacher who became a superintendent herself. The case exploded dramatically in a midsize metropolitan school district, where a principal was arrested on a sex abuse charge. Many colleagues of the principal strongly supported his innocence. Others in the community felt that, it was just a matter of time before he was convicted. The latter view was held by some on the school board, and the superintendent found herself having to address an assumption among some board members that this man was indeed guilty. This view, she recalls, was likely to pre-empt the decision of the courts as the board considered "termination of his employment" prior to his appeal being heard. Each of the issues in this article--all of them raised by superintendents interviewed for this article--has some degree of moral rightness on both sides. While neither side involves outright illegality, one side may intuitively seem more "right" than the other. Superintendents who argue for the side that seems most right may find themselves wondering whether their values are up to date. Many educators agree that such conflicts come with the turf and that worrying about them is part of what it means to be a superintendent. Today's superintendents also sense that the values-driven issues themselves are growing increasingly complex. Asked why, some cite the expansion of new technologies and media structures. Others point to a growing culture of legalism, where administrative decisions are more open to civil rights challenges from students, parents and lawyers. Among the ethical values most frequently mentioned in conversations for this article were fairness, honesty, trust, respect, caring and responsibility. Supplementing them are such tangible, school based attributes as inclusion, equality, justice, open communication and (from the Schools of Integrity research) "open feedback, authentic student input and growth, not punishment. And crucial to a values perspective is a readiness to question rather than to moralize.