For more than a decade, Australian educational systems have been trying to implement curriculum based on an outcomes approach to teaching and learning. A major difficulty in this process has been in applying the approach to the assessment of students’ learning. It has been recognized that teachers require considerably more support in access to information, collection of data, and analysis of data. Much of this support will need to be provided through appropriate computer systems, more than likely using networkable portable devices. Unfortunately research and development into the implementation of such support is in its infancy although the technology is widely available. This chapter describes a pilot project that tested the use of personal digital assistant to collect and analyze assessment data at the point of demonstration of the learning outcome by the student and then provides a background and rationale for continuing research in the area.