For this report, the Chicago teen program, After School Matters, partnered with the American Institutes for Research (AIR) to conduct surveys to understand three key topics as they relate to the unique circumstances of summer 2020: (1) teen experiences, (2) instructor experiences, and (3) program quality. The report compares summer 2020 with previous years and looks ahead to inform future practices. The recommendations are to continue to support basic needs and mental health for teens and instructors, training on facilitating remote learning for instructors, and to focus on teen belonging to help buffer stress.  While these recommendations are for a teen program, the ideas are applicable to a younger afterschool population as well.