Today, digital transformation in higher education reshapes traditional educational systems toward technology-based learning. In the wake of the global pandemic COVID-19, digital transformation has even accelerated at many universities worldwide due to the pressure put on policymakers and university management to adopt educational technology at their institutions to allow education to continue. Using the case of the Open University of Tanzania (OUT), this article discusses critical factors needed for the successful implementation of technology-based learning and other technological innovations like adaptive learning, for example, in higher education in an African context. We applied a Delphi design, a rigorous research method used for structuring a group communication process to allow a group of experts, as a whole, to deal with a complex problem effectively. In total, 24 experts (e.g., instructors, staff, and students) from different regional OUT centres participated in the Delphi study. The paper presents the results of the first round of the Delphi study on the challenges of technology-based learning identified at OUT providing the first insights into the perceived role, probability, and estimated realisation time of adaptive learning at OUT in the future. We argue that not only technological challenges linked to the internet, network, or technological equipment affect the adoption of technology-based learning in higher education, but also that pedagogical, organisational, and global challenges are indispensable for the successful transformation of higher education.