Looking for work is complex. It involves a synthesis of decisions relating to many separate jobseeking tasks, requiring discrimination of how an individual’s skills match the job description, whether the salary offered is acceptable, location of the work and the logistics of arranging suitable transport. These job-seeking tasks are even more difficult for the disabled, and despite the Web Access Initiative (WAI), there are no Web-enabled work searching systems designed as vocational rehabilitation tools. An opportunity exists among the educational technologists to devise a customizable learning platform that can supply a much needed life-long learning resource. It is becoming increasingly obvious that a range of computer supported collaborative learning (CSCL) systems may provide a ubiquitous approach to fulfilling the desire for reskilling the general population. This paper describes a research project in progress, designed to provide an interactive Web-enabled work searching resource for those undergoing vocational rehabilitation.