This management information report provides the Office of Inspector General's (OIG) perspective on challenges the U.S. Department of Education (Department) may face as it implements and oversees the Coronavirus, Aid, Relief, and Economic Security (CARES) Act. In preparing this report, audit work performed by OIG and the Government Accountability Office (GAO) as well as OIG's annual Management Challenges reports were reviewed. OIG also reviewed challenges that the Department faced when administering education-related grant programs funded by the American Recovery and Reinvestment Act (Recovery Act), to include how the challenges were addressed and what lessons were noted as needing to be considered in the event that legislation providing a large yet temporary funding increase for new or existing programs (like the Recovery Act) was enacted in the future. OIG identified challenges related to grantee oversight and monitoring, student financial assistance oversight and monitoring, and data quality and reporting that the Department should consider as it implements and oversees the CARES Act.