For some, the quest for new knowledge is an inherent pastime. Previously, much of what humans learnt was handed down by previous generations. The tools by which this knowledge transfer took place limited to a human-to-human context; where speech and drawings provided the transmission of ideas. However, the implementation of electro-communication tools through the internet is bringing about a global anthropological revolution in human knowledge transfer. Web-based technologies have promoted the concept of learning partnerships and lifelong learning [1], with interest in globalised learning communities gaining momentum [2]. Although there is an expectation that lifelong learning will extend, in a natural sense, into the broader community, thereby promoting learning societies, the current tools are not effectively reaching key sectors of the community such as the special education arena [3]. Furthermore, little is known about the interactive effect of cognitive development and Web-mediated multimedia instruction on performance outcomes in the education and training sectors [4]. This Chapter will discuss a project underway linking Japan and Australia in an intergenerational cross-cultural study. The project is designed to investigate attitudinal changes amongst young children, undergraduate students, and senior citizens, in both synchronous and asynchronous learning environments when engaged in Web-mediated collaborative knowledge sharing activities.