The emergence of Artificial Intelligence (AI) in recent years has provided a myriad of resources and tools to educators, particularly in second language teaching. This chapter explores the potential of chatbots, specifically ChatGPT, to enhance intermediate English learners’ pragmatic competence, focusing on the speech act of complaining. Given that the pragmatic competence entails more than grammatical and lexical accuracy, this study examines how chatbots can help learners assimilate the cultural norms and expectations within the target language and select the most appropriate strategies in determined contexts (Bardovi-Harlig and Mahan-Taylor 2003). Through role plays, ChatGPT enables the modification of contextual variables such as social distance and hierarchy, fostering a meaningful practice in adapting strategies and registers. Although prior research has explored the use of AI in developing the pragmatic competence (Akane et al., Assessing the efficacy of generative Ai in pragmatics: Chatgpt and Japanese learners of Chinese in written apologies, 2024; Puri and Baskara, Proceedings of the international conference on language and language teaching, Rajabhat University, 2023), little attention has been given to the qualitative impact of chatbots on learners’ acquisition of pragmatic strategies. This study evaluates both the pedagogical effectiveness of chatbots in developing complaint strategies and their contribution to autonomous learning through personalisation and instant feedback. Despite certain limitations, the findings suggest that chatbots offer an adaptable environment that supports learners in developing pragmatic routines.