The COVID-19 pandemic forced a rapid shift to online learning, revealing significant challenges for elementary students' foundational academic and emotional development. This study explores the impact of remote learning on students with pre-existing--yet unidentified--attention and mood-related challenges, and aims to shed light on the academic and emotional gaps observed upon the return to in-person learning. To illustrate the extent of observed academic and emotional challenges, two neuropsychological case studies are presented; changes in academic performance, attention, executive function, and emotional well-being, during and after the pandemic, are examined. Findings highlight that, for some students, remote learning catalyzed or exacerbated such challenges. Furthermore, findings underscore the importance of renewed urgency for tailored support and re-evaluation of student needs, regardless of overt risk factors, especially upon returning to traditional school environments. Strategies for academic screening and social-emotional support are proposed as a means to mitigate long-term effects of educational disruptions. It is imperative that future research not only aims to better understand the learning trends observed in this specific cohort, but in the event of inevitable future school disruptions, also endeavors to establish a blueprint for supporting student needs and minimizing educational gaps.