There are two general approaches to supporting collaboration. The first approach consists of structuring the initial conditions in which the collaboration takes place. Factors such as group composition (e.g. accounting for gender or expertise), and the nature of task may help in understanding the nature of potential interaction problems. With regard to technology, a structuring approach involves designing tools that offer affordances for the learner to discover, understand and use in her own thinking (Stahl, this volume). Examples include sentence openers on a dialogue interface or the embodiment of a collaboration script in the learning environment. The second approach consists of coaching and regulating the interaction as it unfolds. Because of the dynamic and unpredictable nature of collaborative learning interaction, it is very difficult to analyze, assess, and coach group learning online. In this chapter, we describe a few different approaches to analyzing and guiding collaboration, and give examples of systems that apply these approaches.