As the pace of digital transformation continues to accelerate in classrooms and myriad distractions vie for the attention of learners, the challenge of engaging students grows ever more daunting (Garet et al., 2020). To establish stimulating learning environments in which students associate positive emotions toward tasks, ascribe value to their activities and become deeply absorbed in their work, thus maximizing their capacity, educators are turning to instructional technology (e.g., iPads) to achieve these critical outcomes. This qualitative case study examined the perceptions of middle school English language arts (ELA) educators and students regarding the effectiveness of iPads in promoting student engagement. Factors that promote and hinder engagement using instructional technology were explored. The data set for this research included: semi-structured interviews, qualitative surveys, student-created multimodal artifacts, Flipgrid-style videos, and related follow-up questions. The study findings aim to inform future instructional practices, as well as further develop strategies for educators who support student-learning with digital tools. [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.]