Digital technology offers several ways to change and fundamentally transform higher education practices. In this chapter, we illuminate digital transformations associated with the use of digital technology to assess student learning. Using qualitative interview data from teachers at two Universities in Sweden, we discuss teachers’ design decisions as they redesigned assignments and courses and introduced automated assessment. The use of digital technology affected teachers’ role and assessment work process in several ways, such as bringing forward and distributing assessment design decisions. We interpreted the possible epistemic consequences of what kind of knowledge teachers assessed with the use of digital technology and found examples of how digital technology facilitated teachers to rethink and create open-ended assignments allowing different ways for students to demonstrate their abilities (divergent assessment). However, against their intentions teachers mainly created pre-defined closed right-or-wrong answers (convergent assessment) resulting in less transparency of student (mis)understanding. Thus, the implementation of digital technology may innovate assessment practices, which in this sense is moving forward. From a pedagogical perspective, teachers’ adaptations of assessment using digital technology imply retrogression rather than innovation regarding how to capture student capabilities.