We report three student groups’ collaboration experiences in a semester-long classroom project. The project included both tasks that required completion in virtual group workspace and activities that could be carried out in the physical world environment. We observed different collaboration patterns among the groups with respect to building and maintaining social relationships, submitting individual work to the group, and scheduling group meetings. We use Bereiter’s two contextual modules, intentional learning and schoolwork, to help us understand the observed patterns and suggest that the group leader’s contextual module plays a significant role in all members’ group learning experiences and outcomes. We propose design implications that are intended for encouraging learning-based (as opposed to work-based) practices in virtual group environments.