This chapter explores how experientially based pedagogical activities that involve participation in real life service encounters provide occasions for developing L2 interactional competence. The data comprises novice L2 students’ self-recorded interactions in service settings and videorecordings of classroom planning activities and de-briefing discussions, where the students reflect on their experiences. The analysis traces what kinds of occasions for learning arise as the students move between the classroom and the real-world service settings. The findings show that the different phases of the task complement each other in supporting the development of interactional competence. The preparation phase enables students to plan initiating actions, but does not prepare them for contingencies of interaction in the wild. When carrying out the task in real world circumstances, occasions for learning can arise as students adapt to the interactional contingencies of the encounter and put their repertoire to use in interaction with others in the full ecology of the activity. Retrospective discussions enable detailed analysis of experiences as well as focused learning activity, whereby the participants develop an experientially based understanding of the interactional tasks, language practices, actions, organization and communicative norms pertaining to the social activity.