The purpose of this multi-case study was to examine the collaborative learning process in two online graduate courses over 13 weeks. The collaboration was assessed through instructors’ and students’ perspectives in terms of what factors successfully supported collaboration, what factors had a negative impact on collaboration, and what recommendations could be made to enhance future experiences. Data were collected from various sources: semi-structured interviews, documentation, synchronous and asynchronous discussion forums, and online observation. Findings from the study identified three essential conditions that were required to support online students’ collaboration: 1) building a safe environment; 2) helping students to feel comfortable; and 3) preparing students for meaningful collaboration. Also, the study identified factors that should be considered in designing online collaborative learning and the necessary structures and scaffolds that need to be in place to support online collaborative learning. Online collaborative learning requires planning, managing, and facilitating.