In response to the COVID-19 pandemic, many governments ordered school closures as a containment measure, with Israel being among over 100 countries to do so. This resulted in the abrupt shift to online and remote education for many students. Despite attempts to minimize the effects of disrupted education and create a dynamic virtual learning environment, the literature highlights various challenges including lack of communication with implications of distress faced by key stakeholders (students and their parents, teachers, and principals). In this cross-sectional study, we assess the perceived levels of communication and psychosocial aspects during both distance and frontal learning, as well as the long-term impacts (following over two and a half years of an ongoing pandemic) on distress among the key stakeholders of the Israeli education system— high school students, parents, teachers, and principals. The study findings demonstrate severe implications of distance learning on communication and psychosocial aspects, with lingering long-term impacts on distress, among all stakeholders (particularly among students). This reveals the need for tailored capacity building and resilience intervention programs to be integrated in the long-term response to the current ongoing pandemic to improve well-being and reduce distress among the various stakeholders, with particular attention to those that are most vulnerable and were hit the hardest.