Education in the Eastern Caribbean has been heavily influenced by the colonial history of the sub-region. In recent years though, in recognition of the fact that the traditional approaches to teaching and learning are no longer meeting the needs of present-day students, there have been calls for change to more student-friendly ones, with electronic technology playing a significant role. However, the resistance to certain types of devices in the classroom has contributed to the slow uptake of widespread use of electronic technology and the online environment as a mode for teaching and learning. The closure of schools due to the advent of COVID-19 pandemic forced education systems in the region to turn to the online environment to engage students in educational activities. Students, teachers and other education officials had to face their apprehensions and venture into this space for schooling. This paper describes actions taken by the Eastern Caribbean Joint Board of Teacher Education to help teachers cope with this different learning environment, guided by the concepts of teacher readiness, equity relating to access of resources and providing caring support for all affected.