One way that language educators can extend a role-play is by adding a complication to encourage the learner say more. This study uses multimodal conversation analysis to explore such obstacles to progressivity among Japanese learners of English at an experiential language learning facility. We first examine an interactional practice in which the educator orients to a learner contribution as misaligned and creates a role-play-specific basis for rejection that expands the sequence, draws attention to linguistic form, and realigns the learner's responses with the task. We then analyze a related practice in which the educator "feigns" a next-turn display of misunderstanding to signal trouble located in some aspect of the learner's prior turn and thereby occasions the learner's reflection on possible pragmatic, syntactic or lexical issues with their contribution. The educators therefore create a temporary interactional barrier that the learner must overcome to progress the sequence. These practices allow the educators to emulate the way that mechanisms like repair, correction and rejection operate in mundane interaction beyond the classroom (i.e., "in the wild") and offer insight into how unscripted role-play tasks can provide opportunities for expanded L2 use.