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The challenges of at-risk students are not new. Newspaper articles from the 1860s presented information about communities seeking to help students to complete school and find employment to provide a livable wage. Today's solutions focus on legislation intended to affect societal change and provide equitable opportunities for at-risk students. Much research regarding how to improve academic outcomes for at-risk students addresses high school level, identifying those factors that encourage secondary learners to remain in school. However, less work has been done investigating whether earlier intervention can obviate later retention efforts by improving students' learning outcomes in the elementary grades. In this vein, engagement is a factor found to positively influence learning, particularly when students are actively engaged with instructional content. Technology can facilitate such interactions between students and content; however, research is needed to better understand the relationship between student engagement and technology, particularly with at-risk students in elementary settings. Seeking to address the gap, this qualitative study examined the occasion of a fifth-grade school that recently implemented 1:1 technology. Using a case study approach, researchers explored the effects of the 1:1 Chromebook implementation on teacher-perceived student engagement at the elementary level. This study sought to better understand how this school technology application influenced student engagement including constructs such as relevance, novelty, and gamification. Teachers in the study expressed that their students' engagement levels increased with Chromebook use. They identified relevance, autonomy, and novelty as reasons for students' engagement with the technology.