This chapter reflects on assessment practices and the potential value that technology offers in this process to both teachers and students in the context of higher education. The positive and negative aspects of integrating technology into the evaluation process are described and what are some factors that serve as a guide to build valuable strategies in the design of an adoption plan for higher education institutions. In the context of the diversification of teaching modalities, both synchronous and asynchronous, this paper highlights how technological innovation in assessment can catalyze positive transformations in student learning. In addition, the revelations of empirical research about teaching experiences with the use of specific technology for evaluation are discussed, proposing strategies aimed at the development of new evaluation paradigms that effectively integrate technology.