Objective/Research Question: How do student- and school-level factors measured in the final year of high school contribute to the odds of a student being assessed to need remediation in Math during the students' first community college enrollment? Methods: The present study draws on five years of linked secondary and post-secondary administrative records and includes the academic records for 18,814 students attending 228 high schools across 24 jurisdictions in Maryland. We used a series of multilevel models (MLM) to address the research question. Results: Using MLM, we identified both student and school-level factors, drawn from the final year of high school, which relate to the odds of needing math remediation in their first year of community college. Of note, student-level academic performance in high school had a larger influence on the odds that a student would need remedial education than socio-demographic factors. In addition, receiving English language learner services and graduating from high school in the fifth-year functioned as protective factors linked to a reduced likelihood of needing math remediation. Conclusions/Contributions: Community colleges are functionally dependent upon secondary schools to prepare the student body for college level coursework. As such, preventing the need for remediation among community college students will not be resolved within institutional siloes and will most probably require some degree of inter-system collaboration. The findings from the current study presents opportunities for early identification and suggest possible targets for intervention intended to reduce the likelihood that high-risk students will need remedial coursework when they arrive at community college.