To address the problem of limited opportunities for practicing second language speaking in interaction, especially delicate interactions requiring pragmatic competence, we describe computer simulations designed for the oral practice of extended pragmatic routines and report on the affordances of such simulations for learning pragmatically appropriate communication. Twelve highly proficient learners of English completed six simulated conversations focused on making requests in academic contexts. Evidence of learning was examined microgenetically by comparing data across the simulated conversations and triangulated by written reflections, surveys, and interviews. Results showed that participants gained content and linguistic forms from expert speaker models, and their interactions in scenario-based simulations indicated greater pragmatic awareness and changes in oral production over time. The majority of participants viewed the program positively, commenting on features such as its authenticity and predictive accuracy.