Online collaborative learning is a complex process as it requires thoughtful and pedagogical considerations regarding the design, implementation, and assessment. To understand online collaborative learning, it is critical to involve stakeholders' perspectives of their lived experiences. A qualitative case study was selected to carry out the investigation. Two online graduate courses were purposefully involved in the study. Data were collected from semi-structured interviews and online observations of students and instructors. The collected data were analyzed using a constant comparative analysis method. The results revealed that multiple proactive supports (i.e., social, pedagogical, and technical support) play critical roles in fostering meaningful collaboration. Instructor presence is an essential factor that enables collaboration to occur as desired through setting the stage, modeling desired expectations, and guiding students to reach expected outcomes. Assessments also have an impact on students' level of engagement; therefore, incorporating both formative and summative assessments for both the product and the process of collaboration is recommended. The findings of this study have implications for online collaboration scaffolding and implementation to support online instructors.