Independent schools are awash in contracts - enrollment contracts, employee contracts, and vendor contracts - and for good reason. By having different parties bound to the school, schools are better able to budget, plan, and forecast their needs. All too often, however, the desire for certainty and security has unintended effects, leaving schools bound to individuals and entities with whom they need to break ties during a crisis to ensure the stability of the institution as a whole. In this session, we review considerations and strategies in drafting contracts to ensure schools are better able to balance the competing needs of certainty and flexibility.