This article examines the qualitative findings from a mixed-methods comparison study of the use of an online multi-user virtual environment called Anytown which supplemented face-to-face writing instruction in a fourth grade classroom to determine implications for the design of such environments and the reported impact of this design on students and teacher. Taking a case-based approach, this study examined the experiences of 44 students in two classrooms in order to detect major differences between the participation of students in a class in which face-to-face instruction was their only means of practicing and receiving feedback on their writing and a second class which provided students with an additional eight hours of opportunity to practice descriptive writing within the Anytown multi-user virtual environment. The main findings suggested that several elements must be present in the design of digital learning environments stemming from literature on using games and learning as a means of encouraging on-task behaviors. Further, it was noted that with a social constructivist design, specific forms of scaffolding that emerge from game context should be developed within the system to encourage student peer cooperation and use of system affordances while reducing reliance on face-to-face direction giving. (Contains 3 tables and 3 figures.)