The improvement of digital resilience and strengthening of information security governance is key to the sustainable operation of healthcare and education institutions. As Taipei Medical University and its affiliate hospitals have grown rapidly over the past years, the need for the hardening of its defenses against increasing security risks is greater than ever. Taipei Medical University has led Asia in being the first medical university to move its entire learning platform onto the cloud, and preparations for moving its hospital information systems (HIS) onto the cloud are also underway. In addition to serving as a leader in the medical field in terms of the adoption and utilization of cloud technologies, the implementation of strategies for the strengthening of the school’s information security defenses against future attacks must also be prioritized. More specifically, questions such as “what preparations must be made to ensure the sustainable operation of core information systems?”, “how can a multi-cloud and hyper-converged infrastructure be used to maximize energy saving and sustainability?”, “how can a universal information security management (ISMS) system be introduced using new cloud infrastructure”, “how to train and bring employees up to date on new security practices”, “how to use digital transformation to drive sustainable development of information systems”, and “how to evaluate and select AI based security products ” need to be answered as the Taipei Medical University continues the shift of services to the cloud. We welcome all those that are interested to join us in the discussion and sharing of experiences on the topic of InfoSec within the medical and educational fields.