The realities of the 21st century have led professors and lecturers to renew their learning assessment practices so that they are more adapted to and contextualized in the current professional world. Despite advances in teaching and learning, assessment methods may still deviate from practice in authentic contexts. Although some instructors are already familiar with more authentic assessments, most are accustomed to using exams as standard practices to test students' achievement of course objectives and essays to prepare students for research or written argumentation. Nevertheless, such typical assessments often lack authenticity and do not develop the full potential of students' 21st-century learning or literacy skills such as communication, creativity, or working with technologies. The past decade has seen the beginnings of a broader reflection on teaching, learning, and evaluating with technologies, including more authentic assessments. In this reflective essay we present how technologies make it possible to diversify assessment methods, resulting in enhanced authenticity and development of 21st-century learning and literacy skills. Authentic assessment methods with technologies (e.g., recorded video presentations, explanatory interviews with descriptive assessment grids, PechaKucha presentations, blog posts, social media and e-portfolios) are illustrated with examples from several disciplines. We also explain how proposing a number of methods to students for the same assessment may help answer their various needs and preferences without increasing instructors' grading load. Furthermore, we discuss how diversifying assessment methods with technologies often results in a transformation of assessment modalities. Beyond assessments as an evaluation of knowledge and/or skills at a fixed time, authentic assessments with technologies may become continuous or iterative processes with multiple feedback occasions from instructors, thereby combining synchronous interactions and/or discussions with asynchronous reflections to improve students' involvement and active learning.