The COVID-19 pandemic has jolted educational organizations and their stakeholders. Mobility between countries is a requisite feature at international schools, with students and educators shifting between home, host, and intermediary countries. Stakeholders are diverse in international schools, representing transcultural interests, giving rise to complex needs and considerations for school leadership. This article explores a subset of data from a study on educator acculturation in international schools that unpacks the effects of, and responses to, the pandemic by sojourning educators at international schools in Southeast and East Asia. Effects on students were not examined. Findings include adaptive responses, mobility barriers and role/school precarity, spikes in acculturative stress, and creative problem-solving. These effects have generated substantial leadership enigmas. Implications include an urgent need to activate adaptive leadership practices, including contingency planning and action research projects aiming at experiential learning from different stakeholder groups in international schools.