The roles of technology and education were at the forefront throughout the COVID-19 pandemic. This mixed-methods study examines the role of the three levels of the digital divide (i.e., access, capability, and outcomes) during the COVID-19 pandemic in Kentucky. We create and analyze a new multifaceted measure of district-level digital capacity to examine the role of prior investments in technological infrastructure and the relationship with student scores in reading, math, and the ACT exam. Increased investment in digital preparedness leading up to the pandemic was protective against decreases in test scores. However, nonmetropolitan and Appalachian areas did not experience the same benefits from their digital capacity investments compared with their metropolitan counterparts. Using interview data from the summer of 2021 with 16 educators predominantly from Appalachian school districts, we discuss why these efforts to bridge the digital divide were hindered by larger, systematic challenges faced by their students.