This paper presents a qualitative analysis of COVID-19′s impact on the development, delivery, and uptake of “Favoring Myself”, a school-based interactive wellness program conducted via Zoom during 2020–2021. “Favoring Myself” targets resilience, self-esteem, body-esteem, self-care behaviors, and media literacy among 5th-grade preadolescents. Data were obtained from meetings, 23 semi-structured interviews with parents, teachers, and principals, and other modes of correspondence. All data were transcribed and thematically analyzed. The analysis highlighted the barriers faced when delivering external programs during COVID-19. Parents’ difficulties in cooperating with the program, distrustful relationships between parents and the education system, as well as teachers’ overload and stress, were identified as barriers to the external program’s sustainability. These challenges are discussed in light of previous studies of school-based programs, the psychological and social contexts of an ongoing crisis and the impact of neoliberalism on education. This study concludes that school-based prevention programs and accompanying research should be more flexible and focus on understanding and relating to parents’ and schools’ fears, uncertainties, and resistance. It is the hope of the authors that knowledge created through this exploration will be helpful in future coping vis-à-vis prevention program teams and recipients in times of unpredictable, unmanageable, and overpowering crises.