There is a common assumption in education that lack of face-to-face instruction during COVID-19 will result in a learning loss when students return to physical classrooms. While some studies reported interesting results on learning loss, more research must be done to inform schooling practices. At a recorded webinar, learning loss was examined by analyzing the ideas of school leaders who manifested deficit-based and/or asset-based views in doing virtual instruction at home. The authors wrote this commentary as a critical reflection of the ideas presented by leaders who reimagined learning gain instead of loss as they recognize, value, and honor the many culturally- and socially-situated knowledge and skills students have acquired and learned during these unprecedented times.