The onset of the SARS Covid-19 coronavirus pandemic in 2020 forced most higher education institutions (HEIs) globally to temporarily discontinue face-to-face operations and migrate most academic and administrative functions to online environments. While some universities have transitioned seamlessly, at least for the most part, others appeared to have been acutely ill-prepared and ill-equipped and have found the task of adapting much more challenging. In this chapter it is argued that differences in the levels of success of attempts by HEIs to digitalize the delivery of education since the Covid-19 pandemic began are largely based on the extent to which HEIs have digital transformation strategic frameworks in place. It is further argued that to achieve success, these frameworks must enable digital readiness, agility, resilience, innovation, and reciprocal satisfaction in the interactions among the networks of internal and external stakeholders involved in their value chains. In this chapter we highlight and evaluate lessons learned from a decade of global experiences with digital transformation. We achieve this through the use of a contextual framework, documentation analysis methodology, and interpretive frameworks. The findings are particularly instructive for HEIs that are operating at different levels of the new digital transformation paradigm.