Despite recovery efforts, not all students have “caught up” for learning opportunities lost during the COVID-19 pandemic, with students belonging to marginalized groups most likely to remain behind pre-COVID-19 trends. Current recovery interventions tend to focus on academic skills and outcomes. Less is known about how students’ home experiences during the pandemic are associated with subsequent engagement. We conducted a descriptive study using survey data from three mid-to-large sized K-12 school districts in the Southeast to examine trends in economic, health, and protective factors experienced by students during the COVID-19 pandemic as well as subsequent associations with changes in student engagement. This is the first large-scale study to examine associations between student engagement and a comprehensive set of COVID-19-related stressors. This more holistic examination of the interplay between individual, family, and systemic factors during and subsequent to the pandemic can be used to better identify, design, and target interventions.