Recent studies of caring school leadership have focused on the way that caring leaders support teachers and influence the school environment. Though caring is understood improve educational outcomes, questions about the interpersonal and organizational enactment can lead to significant disagreements--micropolitical contests. Using case study data, this study examines how leaders' vision of caring leadership shapes micropolitical contests concerning problem-solving and decision-making. The data indicate that schools whose leaders emphasize structured, uniform ideas of caring place pressure on veteran teachers to offer greater support for novice teachers, and cause stress for more inexperienced teachers. At schools where leaders prefer more variable, responsive approaches to care, reduced emphasis on cooperative problem-solving may lead to greater tension around persistent schoolwide problems. The implications of these trade-offs are discussed.