In partnership with the Chan Zuckerberg Initiative and 22 San Mateo County school districts, this report and research brief explore the ways in which local students experience housing instability, and how cross-sector strategies can better identify and serve these students. This study considers a rich set of school administrative data, which allow us to describe youth based on their dwelling status designations reported by the school districts, their free or reduced-price meal participation, and several demographic characteristics. We also examine the relationship between student dwelling status designation and educational outcomes. At a high level, our research finds that over 2,600 adolescents in San Mateo County experienced housing instability over the course of the three school years before the pandemic. Students experiencing housing instability were also: (1) disproportionately Latinx, Black, and/or English language learners; and (2) likely to miss more days of school than their housing stable peers. Based on these findings, we conclude that youth experiencing housing instability face a range of unique challenges, and we recommend a set of concrete actions that state policymakers, local and county leaders, school district leaders, and leaders from youth-serving organizations can take to help ensure positive and equitable outcomes. [This report was written with contributions from Francine Biscocho, Elise Dizon Ross, Kristin Geiser, Amy Gerstein, Leslie Patron, Jayme Pyne, Nicole Tognozzi, and Charlotte Woo. For the report brief, see ED624056.]