In March 2020, schools worldwide suddenly and dramatically transitioned to online learning. This article describes a case study where we used a purposeful sampling of six technology-savvy school principals to explore their experiences with student assessment of learning during the pandemic. Findings captured how these tech-savvy leaders supported teachers, students, and parents and created an infrastructure that prepared them for the transition to online learning and assessment of that learning. The lessons learned are valuable for school leaders who have begun to embrace online and hybrid learning in ways they had not imagined before the pandemic.