Over the last 20 years, writing about technology (and more recently about its use in assessment systems) has been a joyful experience, in part because the author was usually right about how fast and how unexpected technology progress would be made. In this article, the author suggests to rethink assessment systems from design perspectives and the ways in which technology can improve their quality. The author addresses the design of educational assessment systems as well as the potential of new technologies. In the face of acknowledged difficulties, the author attempts to summarize key issues in the present use of and the ideal design and technology support for assessment systems. The author emphasizes how technologies could help with assessment design and implementation, support capacity of teachers, and improve reports. (Contains 3 figures.)