Purpose: This study investigated the roles and perspectives of head teachers and principals in regard to the potential for learning loss in the online setting, with a particular focus on conditions during the coronavirus disease 2019 (COVID-19) pandemic in Kuwait. It also addresses leadership roles and gathered organizational suggestions. Design/methodology/approach: Structured interviews were conducted with 25 head teachers and 6 school principals, while open-ended questionnaires were gathered from 10 head teachers. Both were focused on the potential for learning loss and the reasons it may be induced. More specific subjects included leadership roles in preventing learning loss and suggestions for improvement. All interviews and open-ended questionnaires were transcribed for a subsequent inductive thematic analysis. Findings: Participants reported high levels of learning loss in the context of online teaching during the COVID-19 pandemic. Reasons for this included political decisions made by the Ministry of Education (MoE), student attitudes and the learning environment. Participants also reported substantial involvement in leadership roles aimed at the supervision of online teaching, providing training and support for teachers, and communicating with the administration, district and parents. They also provided several organizational suggestions for reducing learning loss, including the need to improve teaching quality, assess MoE policies, and ensure an ethical online learning environment. Originality/value: The results contribute to a better understanding of learning loss and the leadership roles that are needed to mitigate this issue both in the Middle East and internationally.