Assessment is perhaps the area, like no other, where the utility of information technology in education is tested. The possibilities for assessing using these technologies are expanding rapidly. In particular, new technologies afford possibilities for focusing assessment on learning as an ongoing developmental process, rather than on performance. Building on notions of assessment grounded in measurement theory, there are prospects for assessing students continuously while they learn in a developmental way through the use of data and analytics. The resulting picture of student development will then allow for a more holistic and systemic approach to assessment in the years ahead. While it is often problematic to make predictions about the future, in this chapter, I will attempt to draw on current developments to provide suggestions about where the intersections of assessment and information technologies are likely headed. That future is likely to entail more continuous, personalized forms of assessment that focus heavily on helping students to make better judgments about their own learning and development.