This paper applies the relatively new concept of the Long Tail to classroom environments thereby offering a new way of viewing student participation and engagement. We suggest that Web 2.0 technologies such as forums and wikis will appeal to the Long Tail of low-involvement students to increase their interactions within learning environments in the same way that Internet search and recommendation technologies have enabled firms to capture greater value from the Long Tail of less frequently sold products. This theoretical work contributes to the literature by illustrating how these technologies can offer a simple and efficient means of increasing student participation, engagement and learning. We conclude our concept of Long Tail student engagement with directions for future research and practical suggestions for instructors seeking to employ these technologies in their classrooms.