Significant disproportionality in special education is a persistent problem that has plagued the American public education system for over 50 years. Despite federal, state, and local efforts; this problem has yet to be solved. The persistence of this problem, despite intervention, suggests that significant disproportionality in special education has been viewed as a technical problem with technical interventions being applied, rather than it being viewed as an adaptive challenge requiring an adaptive approach. This study focused on the lived experience of individuals associated with significant disproportionality at the state and local level in Connecticut in order to fully understand the problem within the system. This study included in-depth, semi-structured interviews with four state-level and six district-level participants, as well as document analysis of key written communications related to significant disproportionality in special education. The first theme constructed from the data was Sensemaking and the Impact of Understanding on Approach. This included an awareness of an adaptive approach, the needs of diverse learners, varying levels of understanding, and risks to students from misunderstanding of significant disproportionality. The second theme was Barriers to Collaboration. This included funneled communication, siloed communication, and the need for a whole-district approach. The third theme was Compliance. This included technical interventions, unhelpful compliance tasks, compliance for compliance sake, and the negative perception of the problem. The final theme was the Complexity of the Problem. The Complexity of the problem is unique as it impacts the other themes and vice versa. The four constructed themes offer opportunities to new understanding about significant disproportionality in special education in CT. Analysis revealed a profound technical approach being used at the state and local level. This study demonstrated a connection between the level of sensemaking and understanding of the problem and the type of approach used; the greater the depth of understanding, the more likely an adaptive approach will be used. Analysis also highlighted the strong influence state-level stakeholders have with the approach taken at the local level. This study offers resources and recommendations to support a shift toward an adaptive approach being utilized to reduce significant disproportionality in special education. [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.]