The use of AI for teaching and learning has become the main focus of scholarly attention. Nonetheless, there is a gap in the literature regarding the application of AI-driven tools in the teaching and learning of legal English (LE). Additionally, no academic work has addressed LE teachers’ training in AI-powered tools. Therefore, this contribution is aimed at filling this gap. To this aim, a training session with international LE instructors was organized. The lesson presented several AI-based platforms and applications that could be used in the teaching of LE. Pre- and post-lesson questionnaires were administered to gather information on the teachers’ knowledge and actual usage of AI, as well as to understand their perspectives on intelligent machines, and their impressions on the tools discussed during the lesson. The findings indicate that, prior to the session, LE trainers were not accustomed to relying on AI; materials development was mainly performed manually by using both book- and non-book-based resources. Hence, their knowledge of AI toolkits for the teaching of legal English was limited. Other relevant results show the preponderance of private tuition sessions to academic students, where speaking skills and the knowledge of lexical terminology were the mainstay of their training. Audio-video contents also played a pivotal role in their teaching. The training session allowed LE teachers to become acquainted with AI tools that are specifically designed for the legal field. They also familiarized with other resources that can cater for LE learners’ growing digital needs. At the end of the lesson, participants were equipped with a set of resources that could be readily employed in teaching contexts, thus enhancing digital teaching skills.