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COVID-19 caught the world off-guard, bringing disruption and chaos to all sectors, including education. Within Caribbean Small Island Developing States (SIDS), the experiences were varied, as were the responses of educational stakeholders at all levels to the crisis of the pandemic. Stakeholders' experiences and responses should inform educational planning and policy, and it is against that backdrop that this research was conducted. This research captures the insights from three webinars sponsored by the Caribbean Centre for Educational Planning, which focused on challenges faced by educational institutions at the primary, secondary and tertiary levels of the education system. The transcripts from those webinars were used to construct this paper using a generic qualitative research design. The webinars pulled on the expertise of panelists from across the Caribbean and North America. The findings reveal that most stakeholders were unprepared for the challenges occasioned by COVID-19, which translated into further difficulties adapting to online/blended teaching/learning, psycho-social stresses, heightened economic challenges, and disruptions to examinations. In response to these challenges, among the stakeholders, training was implemented, open communication increased, technical and infrastructural resources were upgraded, health and safety protocols were enforced/reinforced, and domestic and international groups collaborated to bolster access for all students. Lessons learned included the need for collaboration, equity, access, and opportunities, and exercising the courage to radically rethink the region's 'educational futures' by incorporating the shared perspectives of key stakeholders in educational planning and policy making.