In recent years, the school environment has witnessed an increase in the array of crises that are affecting communities, students, and staff. Providing adequate school safety policies and practices has never been such a central focus for federal and local politicians, school leaders, and community members. The importance of addressing school safety is based in the reality that crisis events have long lasting impacts on student and staff engagement, performance, and overall health and wellbeing. The research on school safety planning offers countless strategies and recommendations, but there is a lack of studies that examine the effectiveness of safety policies and practices, and what impact they have on students, staff, and the community. Therefore, the need to examine how schools plan and evaluate comprehensive safety plans is needed. Using a two-phase, comparative case study approach, this study includes a (1) document analysis to determine the components of Comprehensive School Safety Plans (CSSPs) and (2) interviews with school safety committee members to provide context to the planning process and implementation. The study identified how mechanistic structures in CSSP documents can create inequities among school sites as they consider needed resources and services due to standardized practices that lack a process for adjustment. CSSPs that rely too heavily on highly formalized structures are void of the contextual elements that are needed to address and engage with the needs of school communities. This study offers future considerations for school leaders to strengthen the effectiveness of school safety plans and reduce the impact of crisis events on students, staff, and community members. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]