This paper reports on the completion of the first stage of research of a pilot study undertaken in collaboration by 3 Australian universities. The pilot involves the development of a virtual pharmacy patient (VPP) as a study of its effects on student learning when it is used as a formative assessment tool for pharmacy students in interviewing and diagnosing a patient. The design criteria that have been incorporated into the virtual patient system are described. The novelty of this system is in its ability to track and report on the style and appropriateness of student questioning of a virtual pharmacy patient. One of the main problems in this type of system is recognition of free-text student questions. An overview of the pragmatic solution to this and the systems potential as a tool to generate a lexicon for more complex question recognition is presented.