To investigate how college students understand and use cloud technology for collaborative writing, the authors studied two asynchronous online courses, on science communication and on technical communication. Students worked on a group assignment (3–4 per group) using Google Docs and individually reflected on their experience writing collaboratively. This article explores leadership and how it interacts with team knowledge making and the collaborative writing process. Guidelines are outlined for instructors interested in adopting collaborative, cloud-based assignments, and the tension between providing clear instructional guidance for student teams and allowing teams to embrace the ambiguity and messiness of virtual collaboration are discussed.