Although it is widely recognized that exam and assessments are ways to explore and query knowledge, emergence of the internet, digitalization, and the deployment of artificial intelligence in teaching and learning extends the concept to digital exam and assessment. Some lines of research suggest that digital exam and assessments are costly and unfortunate, whereas others suggest that it is beneficial and adaptive. However, there are little theoretical underpinnings probing these arguments. To fill the void, this chapter probe existing teaching and learning literature, and concepts of digital exam and assessments relative to faculty development. To this end, this chapter theorize that these concepts are contingents on generational cohorts, arguments that advances and reorients research on digital exam and assessment, and generational difference are highlighted. The chapter concludes with pros and cons associated with digital assessments.