Despite extensive advocacy and research underscoring the benefits of inclusive education, students with Extensive Support Needs (ESN) continue to be predominantly placed in segregated educational settings, making inclusion a "wicked problem" within the field of education. Wicked problems are characterized by complexity, interconnected challenges, and evolving contexts, necessitating systemic change rather than isolated interventions. This qualitative case study examined one school district's efforts to include kindergarten age students with ESN in general education kindergarten classrooms within their neighborhood schools as part of a broader effort to create an inclusive school system. Case study data were collected through interviews, observations, documents, and a questionnaire and analyzed using Reflexive Thematic Analysis. The findings revealed three primary themes: (1) the inclusion of students with ESN in kindergarten as one component of a broader systemic change effort; (2) an inclusive mindset and the Least Restrictive Environment (LRE) as touchstones for the district's inclusive education efforts; and (3) the strategic importance and impact of kindergarten inclusion. These results suggest that initial efforts to include students with ESN in general education kindergarten classrooms contributed to the development of infrastructure and capacity needed to sustain inclusive practices across the district. The study highlights that while systemic change is essential for achieving sustainable inclusion, early inclusive initiatives may help build the foundation for broader district-wide transformations, supporting the comprehensive and long-term implementation of inclusive education practices. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]