The Pandemic Electronic Benefits Transfer (P-EBT) program was launched as an effort to address the loss of access to free and reduced-price school meals due to widespread school closures at the onset of the COVID-19 pandemic. As schools reopened in a shifting mix of fully virtual, hybrid, and in-person formats and families lacked consistent access to school meals, these benefits were extended through the 2020–21 school year and were highly valuable to families in buffering the full extent of food insecurity they may have faced during this uncertain time. However, the complexity of administering this program was a fundamental barrier in providing timely support to families, who ultimately went without benefits for at least half of the school year. In this report, we dive into the challenges state administrators faced in launching this new program during the 2020–21 school year and reflect on considerations for the future.