The following is a qualitative case study presenting three vignettes exploring the use of language play while microblogging during an academically sanctioned task. Ten students and one teacher used "Twitter" in an intensive, English as a second language advanced grammar course to practice writing sentences with complex grammatical constructions from the academic genre. In turn, the students received occasional corrective feedback from the instructor. Drawing on qualitative data consisting of a corpus of time- and date-stamped tweets, retrospective interviews and discourse analysis of the students' tweets, the author presents three "micro-vignettes" demonstrating how three students responded to contradictions within the original task by qualitatively transforming its context. As a result, they created new learning opportunities, 'spinning-off' (Wertsch, 1998) the microblogging tool, due to the tool's features, the students' previous cultures-of-use, (Thorne, 2003) and their pre-existing social networks (Stefanone & Gay, 2008). The students used Twitter as an instant messaging chat room, moving from the sentence to the utterance (Bakhtin, 1953/1986), embedding target grammar constructions in various forms of ludic language play (Cook, 2000). By dynamically reframing (Goffman, 1974) their own learning activities students took ownership of the task and went through a process of expansive learning (Engëstrom, 2007).