Today, many school districts purchase technology devices for teaching and learning, which provide educators and students opportunities to transform the learning environment. Now more than ever, access to a technology device allows stakeholders to connect, collaborate, and create in ways that were not possible before. With the influx of technology in schools, the need for leadership guidance is critical to ensure technology implementation is effective. Otherwise, districts potentially waste thousands of dollars on devices that are underutilized, and the success of the initiative is hindered. Current research indicates that when principals, or technology directors provide expectations and a vision for technology implementation, higher levels of transformation are exhibited (Brown & Jacobsen, 2016; Hsu, 2016; McLeod et al., 2015; Vyas, 2020). However, minimal literature exists to understand how superintendents influence the success of a 1:1 technology learning initiative. This qualitative multiple case study explored the involvement of two K-12 Texas public school superintendents to understand the impact they had on the success of a 1:1 technology learning initiative. Specifically, I gained insight into each superintendent's technology expectations, vision, communication, and modeling and implementation strategies. Interviews with each superintendent and chief technology officer allowed visibility into how superintendents lead 1:1 technology initiatives. Additionally, I sent a questionnaire to technology staff and principals to gain perspectives on how they felt superintendents influenced the initiative. Following the data collection process, I conducted a within case and cross case analysis, which allowed for emerging themes to be identified. The Transformational Leadership Model (Bass & Riggio, 2008) guided the study and provided a rationale for addressing the main research and sub questions. This study yielded four key findings related to superintendent success in a 1:1 technology initiative. The first finding revealed that superintendents set high expectations for building capacity. Second, each superintendent's vision for technology integration included a growth-mindset and positive culture. Third, superintendents actively communicated their technology vision throughout the school year. Finally, the fourth finding showed superintendents modeled technology usage in their everyday practices. Ultimately, it was evident from this study that the influence of superintendent involvement impacted the 1:1 technology learning initiative. [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.]