This chapter examines the extent to which learners bring a range of pragmatic practices/strategies to the additional-language context which may come from first and additional language/culture resources as they build cultural and linguistic capital. The aim of this chapter is to understand how participants relate and respond to the additional-language interaction. This chapter argues for the concept of transpragmatics. As opposed to merely transferring pragmatic practices, transpragmatics examines how interlocutors adapt existing resources from first and additional language/culture resources to develop new and novel pragmatic ways of interacting. As language users try to make connections through pragmatic processing, transpragmatics reflects a degree of individuality and non-conformity with ‘standard’ additional-language practices as language users navigate through what works and what is effective in a given situation. With a focus on relational work, this chapter examines how language users find their own ways to interpersonally position themselves, especially in terms of closeness/distance and involvement/detachment. Furthermore, it examines how learners can achieve a ‘return’ on investment as they develop cultural and linguistic capital.