The COVID-19 pandemic has given the entire country a crash course in virtual education and digital education platforms. School leaders have been forced to consider a set of very imperfect options as they struggle to reopen their schools. This three-brief collection identifies key issues for school leaders to consider before adopting a digital platform or learning program that will impact curriculum and teaching, student assessment, and privacy/data security. To help ensure that school leaders adopt digital technology that reflects the school’s stated values and goals, the briefs offer recommendations to guide decisions about which digital learning products to choose, how to best use them in the current crisis, and which to abandon when the crisis has passed.