Abstract: The rapid growth of technology has left many schools scrambling in search of the best technology to implement in their classrooms. Tablet devices such as iPads have seen their popularity rise quickly and dramatically. Teachers want their students to have the ability to be more mobile and engaged in the learning process. However, even with the rapid growth of iPad and tablet use, more recent trends are demonstrating that school districts are slowly moving away from tablet devices to cheaper, more cost-effective laptop options, specifically Chromebooks. We employed an instrumental and multiple case study design to examine the technology directors’ tablet or laptop purchase choices at several suburban and public-school districts in the Southern US. We collected data through interviews and surveys. The within-case and cross-case analyses revealed that technology directors often consult district decision makers, but not the students when making purchasing decisions. In one example, a curriculum director chose the district’s technological purchases based on personal preference, rather than technology that would best benefit the district long-term, giving the technology director no choice. We recommend further research in what methods are most effective in determining long-term success when purchasing large amounts of technology.