COVID-19 pandemic has forced technology to evolve as the most challenging means of delivering teaching in addressing the cordon sanitaire. Technology has already been transforming most operation in medical education and secured strong footage in medical schools. NUMed, like any other higher educational institution, has started planning and implementing various strategies to ensure teaching is not hampered during this crisis. ReCaps, online tutorials, discussion boards, online seminars, webinars and quizzes were utilized in reflecting on the current situation. The paper assesses and mitigates the immediate change that has breached the boundaries of students and staffs to be engaged with strategic planning and adoption during the COVID-19 situation. This paper illustrates the interrelatedness and navigates across borders to leverage the possible planning and implementing educational technology as the pedagogical means to ensure the quality of medical education is preserved in fact enhanced through these strategies.