Background: The Summer Food Service Program (SFSP) provides free and nutritious meals to children under age 18 during out-of-school times. During the COVID-19 pandemic, Maryland sponsors served over 9.5 million meals to children through an expanded version of the SFSP. This study aimed to explore and compare the factors that enabled 2 SFSP sponsors in Maryland to dramatically increase meals distribution during the pandemic. Methods: Sponsors were selected based on their responses in the larger study and demographic characteristics of the area in which they served. Semi-structured in-depth interviews were conducted over Zoom--4 interviews with Sponsor A (3 interviews with the sponsor, 1 interview with their vendor) and 1 interview with Sponsor B. Qualitative data were analyzed inductively and deductively. Participation data from 2019 and 2020 were obtained from the Maryland State Department of Education and analyzed. Results: Despite their differences in organization type and geographic region, they identified similar facilitators to their success--communication with the community and utilization of the United States Department of Agriculture-issued waivers. Conclusions: Strengthening community communication networks and permanently integrating more flexibility into regulation of the SFSP may increase meals participation during future out-of-school times.