Online learning programs have been expanding at exponential rates. To help encourage the development of learning communities within these environments, practitioners and scholars are advocating more collaborative learning approaches. Yet, many students express reservations about learning in small groups, particularly online. In this chapter, we explore more deeply the nature of student ambivalence about online collaborative learning. Weaving the findings of case studies of online groups with research and theory in collaborative learning and group dynamics, we argue that students hold on to highly subjective and individualistic understandings of teaching and learning. These perspectives manifest themselves in their overall approach to group inquiry and decision making. To embrace a more interdependent and intersubjective perspective requires a paradigm shift among members with regard to teaching and learning, and a working through of the powerful emotional dynamics associated with group development. We conclude with suggestions for designing and facilitating online environments that addresses these issues.