A foundational component of human interaction is person-to-person understanding through pragmatic behaviors, that is, the expression and understanding of meaning. While pragmatic miscommunications are easily identifiable as they occur, successful pragmatic behavior is not as salient or immediately accessible to learners. Furthermore, immense variety, individual choice, and an increasing number of interactional contexts, make the identification of patterns for communicating and interpreting meaning increasing difficult to define, teach, and assess. However, the affordances of recent technological innovations enable researchers and practitioners the tools to overcome these barriers and, potentially, transform the teaching and learning of languages in, and out, of the classroom. To examine these issues, this presentation will synthesize previous work on the teaching and learning of interlanguage pragmatics as related to digital technologies and then utilize findings from a number of empirical projects to look towards the future.