This qualitative study sought to gather data from secondary school principals to increase understanding of why from their perspective trauma-informed practices have failed to take hold in public secondary schools. Ten secondary school principals in a large urban school district participated in interviews to explore their understanding of chronic trauma, their understanding of how their students have been impacted by trauma, and what they perceive their roles, and the role of their school community should be in addressing chronic trauma for their students. An analysis of the interview data found that the study participants strongly believe that schools should be prepared to address the outcomes of chronic trauma for their students to ensure that students can learn. The study participants discussed broad approaches to addressing chronic trauma; however, there was evidence that a deep understanding of chronic trauma and how to address it was absent for most of the study participants. The study found inadequate professional development and support from the school district for this initiative. As a result, the interview participants’ responses to addressing student trauma were uneven. The school leaders in this study frequently conflated other school initiatives and educational strategies with trauma-informed school practices, demonstrating that initiative fatigue has impacted their ability to fully implement school-wide practices in which all stakeholders are prepared to intervene for student trauma and respond to students who are demonstrating the effects of trauma in a trauma-sensitive fashion. Another significant finding was that the secondary principals faced pressures from competing interests and resistance from their school community, preventing them from prioritizing creating a trauma-informed school. Implications for practice point to the role of school district leadership in ensuring that the conditions exist for school administrators to lead the work of creating sustainable school cultures that are trauma informed. District leadership must take responsibility for their failure to ensure successful school change efforts by creating conditions in which initiative fatigue has become a persistent impediment to improving student outcomes.