Level of Web experience is often a factor for which researchers attempt to control while conducting experimental studies on Web usability. It is typically measured by some means of self-assessment that often includes questions regarding long-term usage, frequency of use, and the types of activities performed while using the Web. A common assumption is that Web experience is the same as Web expertise (high experience = high expertise). In our research studies primarily focused on Web usability and older adults, we found that even when Web experience is controlled, older adults still demonstrated less Web expertise than younger adults. Our research has supported the hypothesis that Web expertise is significantly influenced by how users learned the Web – or their cumulative time spent in collaborative learning environments (learning from and with others) – rather than just how long or how often they have used it. Preliminary results in our labs demonstrate a positive correlation between opportunities for collaborative learning and Web expertise, as well as a negative correlation between opportunities for collaborative learning and age. These results support the need to reassess how best to measure Web expertise and how we might improve Web interaction for older adults.