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New pedagogical models are emerging to attend to the needs of ESL learners who may have to communicate online in their second language. The goal-based scenario approach, as deployed in Columbia Interactive’s American Business Writing program, offers one such solution, allowing students to interact with fictional interlocutors in an online business simulation. Involvement in this learning environment forces students to experience two time frames simultaneously — the learning environment of real-time and the fictional environment of the online scenario. The overlapping of the two environments would seem to problematize the communication of temporal and spatial relations, yet effective business correspondence, where speed and clarity are essential, requires clear temporal anchoring. In this study, I investigate how learners navigate the time frames of a web-enabled learning experience and acquire pragmatic skills. Using assignments submitted in a Columbia Interactive course, I explore temporal practice in an online role-play. The data shows that students leave linguistic tracks of two time streams in their assignments, usually maintaining clear boundaries between the “here-now” of real-time and the “there-then” of scenario time, but occasionally weaving the two in inventive – and pedagogically satisfying – ways.