Over the past decade, social computing has emerged immensely as a phenomenon among distributed communities. The benefits of social systems depend on a large part on the existence of an active user community who use it continuously to deploy and share information. However, while certain systems have enjoyed tremendous success (Facebook, twitter), others have experienced modest adoption at best. It is not clear what factors contribute to the rise and fall of these systems. This paper is a report on our experience with the deployment of a social software tool and our attempts to identify the major barriers to its adoption. We first introduce the system, Gleanr [6], and describe our research methodology. Based on our findings, we propose a set of contextual factors for successful adoption of such tools. While small-scale, our study might provide some insight on how to design social software systems with better chances of wide adoption.