The increased drive towards digital economies, coupled with the transition to online modes of educational access and work during the COVID-19 global pandemic, necessitated a heightened focus on being able to assess digital competencies. Organizations such as the World Economic Forum and Conference Board of Canada state that developing critical thinking and problem-solving skills are vital for individuals to adapt to increasingly digitized and digitalized spaces in a rapidly changing world. The Global Readiness Explorer Project (GREx), a customizable, comprehensive digital toolkit for individuals, institutions, and organizations, offers potential users sets of assessment tools that can provide feedback and insights while using specific indicators regarding digital competency and readiness to engage in fully online learning environments. GREx can also be utilized to develop additional tools to meet the needs of potential users. Utilizing the GREx toolkit, The COVID-19 Teaching and Learning Transition Project (CTLTP) was intended to examine the potential effects of a rapid shift to online teaching and learning at a medium-sized technical university in Ontario. The university espouses a technology-enhanced learning environment using various digital tools. While there were several fully online social and health sciences programs, even before the pandemic, most students learned in physical classrooms and laboratories. This project invited these students, new to fully online learning environments, to participate in responding to three surveys that probed their digital and fully online learning skills and asked about the transition that they experienced during the pandemic. Participants recorded significant negative effects regarding the move to the fully online environment; however, additional research needs to be conducted to determine what lies behind the negative participant perceptions.