While most individuals hope that the COVID-19 viral global pandemic is over, waves of infection and multiple mutating variants persist prompting considerable uncertainty. Re-entering previously familiar routines is especially difficult for youth challenged by excessive intolerance of uncertainty and accompanying anxiety. Therefore, constructing a conceptual map to explain these stressors and a viable skill set to cope with their anxiety are potentially helpful tasks. This is the exact focus of this article. A review of the past and current impact of COVID-19 on children and adolescents’ lives sets the proper context. Intolerance of uncertainty and health anxiety are two core constructs used to understand the psychological impact of the viral outbreak. Consequently, these variables are explained and summarized. A cognitive-behaviorally based toolkit focused on equipping youth experiencing high intolerance of uncertainty and anxious symptoms with skills for re-entry into an uncertain environment is outlined. Various processes and practices are illustrated via a representative confabulated case example.