The COVID-19 pandemic has compelled K-12 schools and districts across the United States to quickly pivot to distance learning. This disruption to traditional in-person instruction required shifts in district leadership and teacher pedagogy. Previous research has shown that teachers must be provided with learning and supportive environments that cultivate and enhance their instructional technology proficiency and capabilities, hence the importance of technology leadership among K-12 administrators (Ertmer, 2005; Ertmer & Ottenbreit-Leftwich, 2010; Hennessy et al., 2005; Hew & Brush, 2007). However, much of the research in the field of K-12 technology integration has relied on quantitative and mixed-methods approaches to reflect their findings. Several gaps in the existing literature have led to a need not only for an in-depth case study approach, but also the need to study the geographic region of New York in the research base. This comparative case study was conducted in two suburban Long Island, New York school districts. The researcher will aim to triangulate findings by utilizing data from teacher focus groups, individual interviews from leaders, and a thorough document analysis of instructional technology plans, teacher contracts, and district websites. The purpose of this comparative case study was to examine the organizational dynamics and leadership practices necessary for an effective K-12 technology integration environment during a time of change. As this study conveys, leadership practices and systems thinking matter. They have been found to have a prominent impact on technology implementation and adaptation within the fabric of K-12 schooling (Christensen, 2018; Raman et al, 2019; Dexter & Richardson, 2020). Given the sudden shift in teaching pedagogy and educational leadership due to a global pandemic, this study aims to stimulate a novel investigation and thorough analysis of its implications on K-12 schools and districts through the lens of key educational stakeholders (e.g., leaders and teachers). Ultimately, the study serves as both a resource and framework to assist the K-12 education community respond to a change process and provide a theoretical framework and research-based actionable steps for educational leaders to utilize as a guide while navigating through shifting teaching and learning landscapes during a time of change. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]