This paper discusses the characteristics of Web 2.0 that differentiate it from the Web of the 1990s. It describes the contextual conditions in which students use the Web today. Furthermore, the paper also examines how Web 2.0’s unique capabilities and youth’s proclivities in using it influence learning and teaching. A stronger research focus on students’ everyday use of Web 2.0 technologies and their learning with Web 2.0 both in and outside of classrooms is needed.