In recent years, interest in and experimentation with generative AI (GenAI) for language analysis, pedagogy, and assessment has raised questions about the relationship between GenAI and second language pragmatics, prompting vibrant discourse at the intersection of linguistics and computer science. Large-language-model–driven chatbots, such as ChatGPT, aim to offer ease and flexibility to users, but is AI truly capable of encompassing and accurately imitating human linguistic behavior? This volume fills a gap in applied linguistic research, where pragmatics has been underexplored in comparison to grammar and vocabulary learning. Two critical questions are explored: Firstly, can GenAI demonstrate human-like pragmatic behavior? Secondly, can GenAI be used effectively to teach and assess the pragmatic competence of second language learners? Integration across chapters supported by empirical data ensure that AI's limitations and practical implications are evaluated appropriately within pragmatics-focused linguistics analysis, instruction, and assessment.