Educators are seeking ways to better engage their students including the use of collaborative virtual learning environments (CVLEs). Some virtual worlds can serve as CVLEs as the advent of Second Life has created particular interest within the education community. Second Life, however, was not initially designed to facilitate education alone. I propose that as a CVLE, Second Life may be failing educators' expectations of its initial, ongoing, and future use as a system for supporting education. In order to determine how Second Life may be failing educators, I conducted a case study with a group of university-level educators that examined their reasons for and against adopting Second Life as a CVLE, the affordances they explored, the barriers they encountered, and how these affordances and barriers affected student learning and the participant's future use of Second Life and future virtual worlds in education. I then compare their use of Second Life to that of traditional groupware systems. As a result, I propose and detail the development of a rich integrated development environment, application programming interface, more flexible privacy policy, and more robust community tools for educators based on these comparisons.