The author explores the technology procurement process in Ontario's publicly funded school districts to determine if it is aligned with relevant research, is grounded in best practices, and enhances student learning. Using a qualitative approach, 10 senior leaders (i.e., chief information officers, superintendents, etc.) were interviewed to reveal the most important factors driving technology acquisition, governance procedures, and assessment measures utilized by school districts in their implementation of educational technology. The data were transcribed and submitted to "computer-assisted NCT analysis" (Friese, 2014). The findings show that senior leaders are making acquisitions that are not aligned with current scholarship, that districts struggle to use data-driven decision-making to support the governance of educational technology spending, and that districts do not have effective assessment measures in place to determine the efficacy of a purchased technology. The study is meant to serve as an informative resource for senior leaders and to present research-based approaches to technology procurement.