The COVID-19 forced shutdown of Jewish preschools (Spring, 2020) presented an unprecedented challenge for schools, preschoolers, and their families. During the preschool years, children are vulnerable to trauma, potentially affecting later adjustment. Relationships between school offerings, preschoolers' school engagement and psychosocial outcomes were explored. Teacher immediacy behaviors were associated with preschoolers' engagement in online learning but not with psychosocial outcomes. There were correlations between students' willingness to engage and actual participation in online education and psychosocial adjustment. This study highlights the role that teachers and schools may play in keeping students connected and engaged in school during times of crisis.