This paper explores the use of emerging Cloud technologies that support real-time online collaboration. It considers the extent to which these technologies can be leveraged to develop complex skillsets supporting interaction between multiple learners in online spaces. In a pilot study that closely examines how groups of learners translate two kinds of collaborative writing tasks, the paper critically investigates some of the positive individual- and group-based strategies that embody effective, genuine online collaboration. Taking into consideration the relationship between the elements of task design, learning experiences and the learning environment, the paper addresses need to come to a fuller understanding of how learners interact in real time and use this understanding to inform future designs in e-learning. (Contains 5 figures.)