Technology devices are increasingly being added by schools as academic resources for students and teachers. These devices are often added with an eye to increasing access and leveling the playing field in terms of digital access. This access is considered by schools to be a competitive advantage, often impacting school rankings and school report card scores. Social scientists, studying the influence of device-for-all policies, often concentrate on quantitative measures, such as student math performance or standardized test scores. Yet, these metrics miss the lived experience in the classroom. As I show in this dissertation, computers are complicated devices, capable of expanding a student’s reach while also adding new obstacles to their day. Drawing on in-depth interviews and 1,400 hours of participant observation, I argue that the everyday experience of using technology within the classroom has the potential – not guarantee – to be good for student performance. However, it is not always good for students’ emotional well-being. With internet connection and high-powered devices, students have more access to information than ever before. And while these devices are powerful teaching tools, some teachers relied on them as replacements for their lesson plans. When students are expected to navigate lessons independently, varying skills and abilities can add additional burdens to their school day. The constant connectivity via digital communication also means that students and teachers are accountable, to a greater degree, to their network (such as parents, bosses, and friends) during the school day. This also comes with increased opportunities for surveillance through social media and digital paper trails captured by students and spread throughout their networks. Paying attention to the everyday impact of connected technology in classrooms, in addition to the impact it has on quantifiable indicators of performance, reveals points of struggle that become difficult for students to escape, and which must be considered as schools evaluate the role of technology within their institutions.