This qualitative investigation explored the social and academic experiences of socially anxious adolescents and young adults in Portugal and the US as they lived through the restrictions imposed by the COVID-19 pandemic. Participants were 10 Portuguese adolescents (mean age = 16.9 years; 50% female) and 7 young adults in the US (mean age = 19.67 years; 71% female; racially/ethnically diverse). Participants completed a semi-structured interview evaluating how the pandemic and social restrictions impacted social anxiety symptoms and associated functional impairment in social and academic domains. Thematic analysis was used to categorize responses across developmental stages and countries. Findings show consistent patterns across cultures, with symptoms of SAD extending to virtual contexts. Participants reported avoidance behaviors that were reinforced by social distancing mandates and declines in academic engagement during remote learning. Anticipatory anxiety about the return to normal social routines was also evident. Schools should be aware of the impact of social confinement on socially anxious students as they return to in person school schedules and social demands.