The COVID-19 school closures offered states and local school districts an opportunity to reimagine education--to tailor it to meet students' needs, support teachers and aid their professional development, keep schools safe, and better support families. Thus far, not a lot of imagination is on display. In particular, schools are not taking advantage of the tremendous opportunities that technology provides--or at least have not made them available to all students. The authors predict that even if school looks more like "normal" in fall 2021, schools will at some point need to rely on virtual learning again. State boards of education should therefore start now to imagine and plan for Virtual School 2.0. State boards have varying levels of authority to accomplish this task, yet all have the power of the question. This article offers five questions: (1) How well have students been served by remote learning, and are there significant gaps between groups?; (2) Can technology help reduce disparities in student learning?; (3) How can technology help teachers personalize learning?; (4) How can technology keep teachers and students safe when they return to school?; and (5) Are students and educators safe in a digital learning environment?