The rapid incursion of ICT into the classroom has meant that, within a space of a few years, computers have moved from being peripheral to being an integral part of the learning environment. However, our perceptions of a technology are affected by the age at which we encounter it. This chapter draws on the findings of a number of research projects at the University of Sheffield. These findings are used to explore some of the ’generation gaps’ that arise from differing perceptions of learning technologies. The data discussed provide insights into the ICT-based generation gaps that currently exist between and within groups of students, teachers and parents. It is argued that a fundamental gap may exist between students differing in age by as little as five years. Results from a related project exploring Networked Information and Communication Literacy Skills (NICLS), are used to introduce a discussion on the nature of any skills gap that must be addressed in the light of these generation gaps.